ACS Publications. Most Trusted. Most Cited. Most Read
CONTENT TYPES

Figure 1Loading Img

Tri(1-adamantyl)phosphine: Expanding the Boundary of Electron-Releasing Character Available to Organophosphorus Compounds

View Author Information
Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States
Cite this: J. Am. Chem. Soc. 2016, 138, 20, 6392–6395
Publication Date (Web):May 10, 2016
https://doi.org/10.1021/jacs.6b03215
Copyright © 2016 American Chemical Society
Subscribed Access
Article Views
11047
Altmetric
-
Citations
LEARN ABOUT THESE METRICS
Read OnlinePDF (902 KB) OpenURL UNIV OF HOUSTON MAIN
Supporting Info (3)»

Abstract

Abstract Image

We report here the remarkable properties of PAd3, a crystalline air-stable solid accessible through a scalable SN1 reaction. Spectroscopic data reveal that PAd3, benefiting from the polarizability inherent to large hydrocarbyl groups, exhibits unexpected electron releasing character that exceeds other alkylphosphines and falls within a range dominated by N-heterocyclic carbenes. Dramatic effects in catalysis are also enabled by PAd3 during Suzuki–Miyaura cross-coupling of chloro(hetero)arenes (40 examples) at low Pd loading, including the late-stage functionalization of commercial drugs. Exceptional space-time yields are demonstrated for the syntheses of industrial precursors to valsartan and boscalid from chloroarenes with ∼2 × 104 turnovers in 10 min.

Supporting Information

ARTICLE SECTIONS
Jump To

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.6b03215.

  • Experimental details and data (PDF)

  • Crystallographic data (CIF)

  • Crystallographic data (CIF)

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By


This article is cited by 91 publications.

  1. Jingjun Huang, Matthew Isaac, Ryan Watt, Joseph Becica, Emma Dennis, Makhsud I. Saidaminov, William A. Sabbers, David C. Leitch. DMPDAB–Pd–MAH: A Versatile Pd(0) Source for Precatalyst Formation, Reaction Screening, and Preparative-Scale Synthesis. ACS Catalysis 2021, 11 (9) , 5636-5646. https://doi.org/10.1021/acscatal.1c00288OpenURL UNIV OF HOUSTON MAIN
  2. Julia M. Stauber, Arnold L. Rheingold, Alexander M. Spokoyny. Gold(III) Aryl Complexes as Reagents for Constructing Hybrid Peptide-Based Assemblies via Cysteine S-Arylation. Inorganic Chemistry 2021, 60 (7) , 5054-5062. https://doi.org/10.1021/acs.inorgchem.1c00087OpenURL UNIV OF HOUSTON MAIN
  3. Benjamin Murray, Shibin Zhao, James M. Aramini, Hsin Wang, Mark R. Biscoe. The Stereochemical Course of Pd-Catalyzed Suzuki Reactions Using Primary Alkyltrifluoroborate Nucleophiles. ACS Catalysis 2021, 11 (5) , 2504-2510. https://doi.org/10.1021/acscatal.0c04325OpenURL UNIV OF HOUSTON MAIN
  4. Alison M. Wilders, Jeremy Henle, Michael C. Haibach, Rafal Swiatowiec, Jeffrey Bien, Rodger F. Henry, Shardrack O. Asare, Amanda L. Wall, Shashank Shekhar. Pd-Catalyzed Cross-Coupling of Hindered, Electron-Deficient Anilines with Bulky (Hetero)aryl Halides Using Biaryl Phosphorinane Ligands. ACS Catalysis 2020, 10 (24) , 15008-15018. https://doi.org/10.1021/acscatal.0c04280OpenURL UNIV OF HOUSTON MAIN
  5. Shu-kai Liu, Wen-Ching Chen, Glenn P. A. Yap, Tiow-Gan Ong. Synthesis of Carbophosphinocarbene and Their Donating Ability: Expansion of the Carbone Class. Organometallics 2020, 39 (23) , 4395-4401. https://doi.org/10.1021/acs.organomet.0c00618OpenURL UNIV OF HOUSTON MAIN
  6. Fumiya Hirakawa, Hiroshi Nakagawa, Shunya Honda, Shintaro Ishida, Takeaki Iwamoto. Trialkylphosphines Having a Bulky Phosphacyclopentane Backbone: Structural and Redox Properties Depending on the Exocyclic Alkyl Groups and EPR Observation of a Persistent Trialkylphosphine Radical Cation. The Journal of Organic Chemistry 2020, 85 (22) , 14634-14642. https://doi.org/10.1021/acs.joc.0c01393OpenURL UNIV OF HOUSTON MAIN
  7. Shin Ando, Mio Otsuka, Tadao Ishizuka. Analyses of the Structural and Electronic Properties of NHCs with Bicyclic Architectures. Organometallics 2020, 39 (21) , 3839-3848. https://doi.org/10.1021/acs.organomet.0c00564OpenURL UNIV OF HOUSTON MAIN
  8. Koji Kubota, Rikuro Takahashi, Minami Uesugi, Hajime Ito. A Glove-Box- and Schlenk-Line-Free Protocol for Solid-State C–N Cross-Coupling Reactions Using Mechanochemistry. ACS Sustainable Chemistry & Engineering 2020, 8 (44) , 16577-16582. https://doi.org/10.1021/acssuschemeng.0c05834OpenURL UNIV OF HOUSTON MAIN
  9. Anna Wrona-Piotrowicz, Anna Makal, Janusz Zakrzewski. Triflic Acid-Promoted Adamantylation and tert-Butylation of Pyrene: Fluorescent Properties of Pyrene-Decorated Adamantanes and a Channeled Crystal Structure of 1,3,5-Tris(pyren-2-yl)adamantane. The Journal of Organic Chemistry 2020, 85 (17) , 11134-11139. https://doi.org/10.1021/acs.joc.0c01060OpenURL UNIV OF HOUSTON MAIN
  10. Antony Obanda, Kendra Valerius, Joel T. Mague, Stephen Sproules, James P. Donahue. Group 10 Metal Dithiolene Bis(isonitrile) Complexes: Synthesis, Structures, Properties, and Reactivity. Organometallics 2020, 39 (15) , 2854-2870. https://doi.org/10.1021/acs.organomet.0c00375OpenURL UNIV OF HOUSTON MAIN
  11. Thomas Barber, Stephen P. Argent, Liam T. Ball. Expanding Ligand Space: Preparation, Characterization, and Synthetic Applications of Air-Stable, Odorless Di-tert-alkylphosphine Surrogates. ACS Catalysis 2020, 10 (10) , 5454-5461. https://doi.org/10.1021/acscatal.0c01414OpenURL UNIV OF HOUSTON MAIN
  12. Peter Viereck, Simon Krautwald, Tyler P. Pabst, Paul J. Chirik. A Boron Activating Effect Enables Cobalt-Catalyzed Asymmetric Hydrogenation of Sterically Hindered Alkenes. Journal of the American Chemical Society 2020, 142 (8) , 3923-3930. https://doi.org/10.1021/jacs.9b12214OpenURL UNIV OF HOUSTON MAIN
  13. Yumeela Ganga-Sah, Daniel B. Leznoff, Andrew J. Bennet. Synthesis of Sterically Congested 2,2′-Bi(Adamantyl)-Based Alcohol and Amines. The Journal of Organic Chemistry 2019, 84 (23) , 15276-15282. https://doi.org/10.1021/acs.joc.9b02293OpenURL UNIV OF HOUSTON MAIN
  14. Yi-Chi Yang, Yi-Ching Lin, Yen-Ku Wu. Palladium-Catalyzed Cascade Arylation of Vinylogous Esters Enabled by Tris(1-adamantyl)phosphine. Organic Letters 2019, 21 (23) , 9286-9290. https://doi.org/10.1021/acs.orglett.9b03071OpenURL UNIV OF HOUSTON MAIN
  15. Yuuki Sawatsugawa, Ken Tamura, Natsuhiro Sano, Tsuneo Imamoto. A Bulky Three-Hindered Quadrant Bisphosphine Ligand: Synthesis and Application in Rhodium-Catalyzed Asymmetric Hydrogenation of Functionalized Alkenes. Organic Letters 2019, 21 (22) , 8874-8878. https://doi.org/10.1021/acs.orglett.9b02702OpenURL UNIV OF HOUSTON MAIN
  16. Chunming Zhang, Kelli Ogawa, Siyu Tu, Chengli Zu, Jim Ringer, Chris Derstine, Hien Do, Philip P. Fontaine, Jerzy Klosin. Highly Active Monoligated Arylpalladacyles for Cross-Coupling Reactions. Organic Process Research & Development 2019, 23 (10) , 2181-2190. https://doi.org/10.1021/acs.oprd.9b00234OpenURL UNIV OF HOUSTON MAIN
  17. Thorsten Scherpf, Ilja Rodstein, Maurice Paaßen, Viktoria H. Gessner. Group 9 and 10 Metal Complexes of an Ylide-Substituted Phosphine: Coordination versus Cyclometalation and Oxidative Addition. Inorganic Chemistry 2019, 58 (12) , 8151-8161. https://doi.org/10.1021/acs.inorgchem.9b00948OpenURL UNIV OF HOUSTON MAIN
  18. Lei Wang, Yi-Ming Wei, Yan Zhao, Xin-Fang Duan. Unified Protocol for Fe-Based Catalyzed Biaryl Cross-Couplings between Various Aryl Electrophiles and Aryl Grignard Reagents. The Journal of Organic Chemistry 2019, 84 (9) , 5176-5186. https://doi.org/10.1021/acs.joc.9b00151OpenURL UNIV OF HOUSTON MAIN
  19. Louis-Charles Campeau, Nilay Hazari. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future. Organometallics 2019, 38 (1) , 3-35. https://doi.org/10.1021/acs.organomet.8b00720OpenURL UNIV OF HOUSTON MAIN
  20. Shin Ando, Ryota Miyata, Hirofumi Matsunaga, Tadao Ishizuka. Influences of Phenyl Rings on NHC Ligands with Bicyclic Architectures. The Journal of Organic Chemistry 2019, 84 (1) , 128-139. https://doi.org/10.1021/acs.joc.8b02480OpenURL UNIV OF HOUSTON MAIN
  21. Yiming Zhao, Huy van Nguyen, Louise Male, Philip Craven, Benjamin R. Buckley, John S. Fossey. Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling. Organometallics 2018, 37 (22) , 4224-4241. https://doi.org/10.1021/acs.organomet.8b00539OpenURL UNIV OF HOUSTON MAIN
  22. Amanda K. Leone, Emily A. Mueller, Anne J. McNeil. The History of Palladium-Catalyzed Cross-Couplings Should Inspire the Future of Catalyst-Transfer Polymerization. Journal of the American Chemical Society 2018, 140 (45) , 15126-15139. https://doi.org/10.1021/jacs.8b09103OpenURL UNIV OF HOUSTON MAIN
  23. Klaus Banert, Manuel Heck, Andreas Ihle, Julia Kronawitt, Tom Pester, Tharallah Shoker. Steric Hindrance Underestimated: It is a Long, Long Way to Tri-tert-alkylamines. The Journal of Organic Chemistry 2018, 83 (9) , 5138-5148. https://doi.org/10.1021/acs.joc.8b00496OpenURL UNIV OF HOUSTON MAIN
  24. Liye Chen, Haydn Francis, Brad P. Carrow. An “On-Cycle” Precatalyst Enables Room-Temperature Polyfluoroarylation Using Sensitive Boronic Acids. ACS Catalysis 2018, 8 (4) , 2989-2994. https://doi.org/10.1021/acscatal.8b00341OpenURL UNIV OF HOUSTON MAIN
  25. Jie Dong, Hui Guo, and Qiao-Sheng Hu . Controlled Pd(0)/Ad3P-Catalyzed Suzuki Cross-Coupling Polymerization of AB-Type Monomers with Ad3P-Coordinated Acetanilide-Based Palladacycle Complex as Initiator. ACS Macro Letters 2017, 6 (11) , 1301-1304. https://doi.org/10.1021/acsmacrolett.7b00759OpenURL UNIV OF HOUSTON MAIN
  26. Dong-Dong Lu, Xu-Xian He, and Feng-Shou Liu . Bulky Yet Flexible Pd-PEPPSI-IPentAn for the Synthesis of Sterically Hindered Biaryls in Air. The Journal of Organic Chemistry 2017, 82 (20) , 10898-10911. https://doi.org/10.1021/acs.joc.7b01711OpenURL UNIV OF HOUSTON MAIN
  27. Liye Chen, Daniel R. Sanchez, Bufan Zhang, and Brad P. Carrow . “Cationic” Suzuki–Miyaura Coupling with Acutely Base-Sensitive Boronic Acids. Journal of the American Chemical Society 2017, 139 (36) , 12418-12421. https://doi.org/10.1021/jacs.7b07687OpenURL UNIV OF HOUSTON MAIN
  28. David A. Petrone, Ivan Franzoni, Juntao Ye, José F. Rodríguez, Amalia I. Poblador-Bahamonde, and Mark Lautens . Palladium-Catalyzed Hydrohalogenation of 1,6-Enynes: Hydrogen Halide Salts and Alkyl Halides as Convenient HX Surrogates. Journal of the American Chemical Society 2017, 139 (9) , 3546-3557. https://doi.org/10.1021/jacs.7b00482OpenURL UNIV OF HOUSTON MAIN
  29. James D. Nobbs, Choon Heng Low, Ludger P. Stubbs, Cun Wang, Eite Drent, and Martin van Meurs . Isomerizing Methoxycarbonylation of Alkenes to Esters Using a Bis(phosphorinone)xylene Palladium Catalyst. Organometallics 2017, 36 (2) , 391-398. https://doi.org/10.1021/acs.organomet.6b00813OpenURL UNIV OF HOUSTON MAIN
  30. Xiao-Bing Lan, Fu-Min Chen, Bei-Bei Ma, Dong-Sheng Shen, and Feng-Shou Liu . Pd-PEPPSI Complexes Bearing Bulky [(1,2-Di-(tert-butyl)acenaphthyl] (DtBu-An) on N-Heterocarbene Backbones: Highly Efficient for Suzuki–Miyaura Cross-Coupling under Aerobic Conditions. Organometallics 2016, 35 (22) , 3852-3860. https://doi.org/10.1021/acs.organomet.6b00723OpenURL UNIV OF HOUSTON MAIN
  31. Allen L. Chan, Jess Estrada, Christos E. Kefalidis, and Vincent Lavallo . Changing the Charge: Electrostatic Effects in Pd-Catalyzed Cross-Coupling. Organometallics 2016, 35 (19) , 3257-3260. https://doi.org/10.1021/acs.organomet.6b00622OpenURL UNIV OF HOUSTON MAIN
  32. Oana Moncea, Maria A. Gunawan, Didier Poinsot, Hélène Cattey, Jonathan Becker, Raisa I. Yurchenko, Ekaterina D. Butova, Heike Hausmann, Marina Šekutor, Andrey A. Fokin, Jean-Cyrille Hierso, and Peter R. Schreiner . Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines. The Journal of Organic Chemistry 2016, 81 (19) , 8759-8769. https://doi.org/10.1021/acs.joc.6b01219OpenURL UNIV OF HOUSTON MAIN
  33. Sean McCarthy, D. Christopher Braddock, James D.E.T. Wilton-Ely. Strategies for sustainable palladium catalysis. Coordination Chemistry Reviews 2021, 442 , 213925. https://doi.org/10.1016/j.ccr.2021.213925OpenURL UNIV OF HOUSTON MAIN
  34. Heidar Darmandeh, Julian Löffler, Nikolaos V. Tzouras, Busra Dereli, Thorsten Scherpf, Kai‐Stephan Feichtner, Sofie Vanden Broeck, Kristof Van Hecke, Marina Saab, Catherine S. J. Cazin, Luigi Cavallo, Steven P. Nolan, Viktoria H. Gessner. Au⋅⋅⋅H−C Hydrogen Bonds as Design Principle in Gold(I) Catalysis. Angewandte Chemie 2021, https://doi.org/10.1002/ange.202108581OpenURL UNIV OF HOUSTON MAIN
  35. Heidar Darmandeh, Julian Löffler, Nikolaos V. Tzouras, Busra Dereli, Thorsten Scherpf, Kai‐Stephan Feichtner, Sofie Vanden Broeck, Kristof Van Hecke, Marina Saab, Catherine S. J. Cazin, Luigi Cavallo, Steven P. Nolan, Viktoria H. Gessner. Au⋅⋅⋅H−C Hydrogen Bonds as Design Principle in Gold(I) Catalysis. Angewandte Chemie International Edition 2021, https://doi.org/10.1002/anie.202108581OpenURL UNIV OF HOUSTON MAIN
  36. Robin F. Weitkamp, Beate Neumann, Hans‐Georg Stammler, Berthold Hoge. Phosphorus‐Containing Superbases: Recent Progress in the Chemistry of Electron‐Abundant Phosphines and Phosphazenes. Chemistry – A European Journal 2021, 27 (42) , 10807-10825. https://doi.org/10.1002/chem.202101065OpenURL UNIV OF HOUSTON MAIN
  37. Asanda C. Matsheku, Richard Tia, Munaka C. Maumela, Banothile C. E. Makhubela. Ferrocenylimine Palladium (II) Complexes: Synthesis, Characterization and Application in Mizoroki-Heck and Suzuki-Miyaura Cross-Coupling Reactions. Catalysts 2021, 11 (7) , 755. https://doi.org/10.3390/catal11070755OpenURL UNIV OF HOUSTON MAIN
  38. Koji Kubota, Hajime Ito. Development of Selective Reactions Using Ball Milling. Journal of Synthetic Organic Chemistry, Japan 2021, 79 (5) , 492-502. https://doi.org/10.5059/yukigoseikyokaishi.79.492OpenURL UNIV OF HOUSTON MAIN
  39. Jens Handelmann, Chatla Naga Babu, Henning Steinert, Christopher Schwarz, Thorsten Scherpf, Alexander Kroll, Viktoria H. Gessner. Towards the rational design of ylide-substituted phosphines for gold( i )-catalysis: from inactive to ppm-level catalysis. Chemical Science 2021, 12 (12) , 4329-4337. https://doi.org/10.1039/D1SC00105AOpenURL UNIV OF HOUSTON MAIN
  40. Michael V. Bautista, Anthony J. Varni, Josué Ayuso-Carrillo, Matthew C. Carson, Kevin J. T. Noonan. Pairing Suzuki–Miyaura cross-coupling and catalyst transfer polymerization. Polymer Chemistry 2021, 12 (10) , 1404-1414. https://doi.org/10.1039/D0PY01507EOpenURL UNIV OF HOUSTON MAIN
  41. Uwaila Omoruyi, Samuel J. Page, Samantha L. Apps, Andrew J.P. White, Nicholas J. Long, Philip W. Miller. Synthesis and characterisation of a range of Fe, Co, Ru and Rh triphos complexes and investigations into the catalytic hydrogenation of levulinic acid. Journal of Organometallic Chemistry 2021, 935 , 121650. https://doi.org/10.1016/j.jorganchem.2020.121650OpenURL UNIV OF HOUSTON MAIN
  42. Nicholas A. Richard, Chun Keat Khor, Sydney M. Hetherington, Scott L. Mills, Andreas Decken, C. Adam Dyker. Iminophosphorano‐Substituted Bispyridinylidenes: Redox Potentials and Substituent Constants from Tolman Electronic Parameters. Chemistry – A European Journal 2020, 26 (72) , 17371-17375. https://doi.org/10.1002/chem.202004153OpenURL UNIV OF HOUSTON MAIN
  43. Awal Noor, Sadaf Qayyum, Sher Ali Khan. Synthesis and Structure of 1,2-Bis(2,6-dimethylphenylphosphino)ethane: A Missing Member of the Phosphine Family. Journal of Chemical Crystallography 2020, 50 (4) , 438-442. https://doi.org/10.1007/s10870-019-00801-9OpenURL UNIV OF HOUSTON MAIN
  44. Matthew R. Espinosa, Angelino Doppiu, Nilay Hazari. Differences in the Performance of Allyl Based Palladium Precatalysts for Suzuki‐Miyaura Reactions. Advanced Synthesis & Catalysis 2020, 362 (22) , 5062-5078. https://doi.org/10.1002/adsc.202000987OpenURL UNIV OF HOUSTON MAIN
  45. Xinlan A. F. Cook, Antoine Gombert, Janette McKnight, Loïc R. E. Pantaine, Michael C. Willis. The 2‐Pyridyl Problem: Challenging Nucleophiles in Cross‐Coupling Arylations. Angewandte Chemie 2020, 8 https://doi.org/10.1002/ange.202010631OpenURL UNIV OF HOUSTON MAIN
  46. Xinlan A. F. Cook, Antoine Gombert, Janette McKnight, Loïc R. E. Pantaine, Michael C. Willis. The 2‐Pyridyl Problem: Challenging Nucleophiles in Cross‐Coupling Arylations. Angewandte Chemie International Edition 2020, 8 https://doi.org/10.1002/anie.202010631OpenURL UNIV OF HOUSTON MAIN
  47. Thorsten Scherpf, Henning Steinert, Angela Großjohann, Katharina Dilchert, Jens Tappen, Ilja Rodstein, Viktoria H. Gessner. Efficient Pd‐Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents. Angewandte Chemie 2020, 132 (46) , 20777-20784. https://doi.org/10.1002/ange.202008866OpenURL UNIV OF HOUSTON MAIN
  48. Thorsten Scherpf, Henning Steinert, Angela Großjohann, Katharina Dilchert, Jens Tappen, Ilja Rodstein, Viktoria H. Gessner. Efficient Pd‐Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents. Angewandte Chemie International Edition 2020, 59 (46) , 20596-20603. https://doi.org/10.1002/anie.202008866OpenURL UNIV OF HOUSTON MAIN
  49. Xinghua Ma, Benjamin Murray, Mark R. Biscoe. Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles. Nature Reviews Chemistry 2020, 4 (11) , 584-599. https://doi.org/10.1038/s41570-020-00222-9OpenURL UNIV OF HOUSTON MAIN
  50. Vladislav A. Voloshkin, Marina Saab, Kristof Van Hecke, Sii Hong Lau, Bradley P. Carrow, Steven P. Nolan. Synthesis, reactivity and catalytic activity of Au-PAd 3 complexes. Dalton Transactions 2020, 49 (39) , 13872-13879. https://doi.org/10.1039/D0DT03330HOpenURL UNIV OF HOUSTON MAIN
  51. Janina A. Werra, Marius A. Wünsche, Patrick Rathmann, Paul Mehlmann, Pawel Löwe, Fabian Dielmann. Effective Control of the Electron‐donating Ability of Phosphines by using Phosphazenyl and Phosphoniumylidyl Substituents. Zeitschrift für anorganische und allgemeine Chemie 2020, 646 (13) , 794-799. https://doi.org/10.1002/zaac.202000028OpenURL UNIV OF HOUSTON MAIN
  52. Kevin H. Shaughnessy. Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions. Current Organic Chemistry 2020, 24 (3) , 231-264. https://doi.org/10.2174/1385272824666200211114540OpenURL UNIV OF HOUSTON MAIN
  53. Yu-Hsuan Chang, Wan-Ling Peng, I-Chia Chen, Hsin-Yun Hsu, Yen-Ku Wu. Palladium-catalyzed α-arylation of indolin-3-ones. Chemical Communications 2020, 56 (34) , 4660-4663. https://doi.org/10.1039/D0CC00435AOpenURL UNIV OF HOUSTON MAIN
  54. Luis Daniel Sifuentes-Vázquez, Eduardo Martínez-González, Rubén A. Toscano, Rubén Gaviño, Jorge Cárdenas, Carlos Antonio Rius-Alonso, Carlos Amador-Bedolla, Gustavo Alberto García de la Mora, Victor Manuel Ugalde-Saldivar. Experimental and Theoretical Exploration of Aryl Substituent Effects on the Electronic Properties of Asymmetric 4,7-Di(thiophene-2-yl)-benzo[c][2,1,5]thiadiazole Compounds. Polycyclic Aromatic Compounds 2020, , 1-16. https://doi.org/10.1080/10406638.2020.1749858OpenURL UNIV OF HOUSTON MAIN
  55. Jens Tappen, Ilja Rodstein, Katie McGuire, Angela Großjohann, Julian Löffler, Thorsten Scherpf, Viktoria H. Gessner. Palladium Complexes Based on Ylide‐Functionalized Phosphines (YPhos): Broadly Applicable High‐Performance Precatalysts for the Amination of Aryl Halides at Room Temperature. Chemistry – A European Journal 2020, 26 (19) , 4281-4288. https://doi.org/10.1002/chem.201905535OpenURL UNIV OF HOUSTON MAIN
  56. Ádám Sinai, Dániel Cs. Simkó, Fruzsina Szabó, Attila Paczal, Tamás Gáti, Attila Bényei, Zoltán Novák, András Kotschy. Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application. European Journal of Organic Chemistry 2020, 2020 (9) , 1122-1128. https://doi.org/10.1002/ejoc.201901834OpenURL UNIV OF HOUSTON MAIN
  57. Erfei Wang, Jiawei Zhang, Zhuoran Zhong, Kaixuan Chen, Mao Chen. Shuttling Catalyst: Facilitating C−C Bond Formation via Cross‐Couplings with a Thermoresponsive Polymeric Ligand. Israel Journal of Chemistry 2020, 60 (3-4) , 419-423. https://doi.org/10.1002/ijch.201900143OpenURL UNIV OF HOUSTON MAIN
  58. Lukas F.B. Wilm, Paul Mehlmann, Florenz Buß, Fabian Dielmann. Synthesis and characterization of strongly electron-donating bidentate phosphines containing imidazolin-2-ylidenamino substituents and their electron-rich nickel(0), palladium(II) and gold(I) chelate complexes. Journal of Organometallic Chemistry 2020, 909 , 121097. https://doi.org/10.1016/j.jorganchem.2019.121097OpenURL UNIV OF HOUSTON MAIN
  59. Kevin H. Shaughnessy. Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active Species. Israel Journal of Chemistry 2020, 60 (3-4) , 180-194. https://doi.org/10.1002/ijch.201900067OpenURL UNIV OF HOUSTON MAIN
  60. Yu Tang, Biao Yu. Coinage Metal (Bisfluorosulfonyl)imide Complexes: Preparation, Characterization, and Catalytic Applications. European Journal of Inorganic Chemistry 2020, 2020 (1) , 107-118. https://doi.org/10.1002/ejic.201901058OpenURL UNIV OF HOUSTON MAIN
  61. Philipp Rotering, Lukas F. B. Wilm, Janina A. Werra, Fabian Dielmann. Pyridinylidenaminophosphines: Facile Access to Highly Electron‐Rich Phosphines. Chemistry – A European Journal 2020, 26 (2) , 406-411. https://doi.org/10.1002/chem.201904621OpenURL UNIV OF HOUSTON MAIN
  62. Seewon Joung, Allison M. Bergmann, M. Kevin Brown. Ni-catalyzed 1,2-benzylboration of 1,2-disubstituted unactivated alkenes. Chemical Science 2019, 10 (47) , 10944-10947. https://doi.org/10.1039/C9SC04199KOpenURL UNIV OF HOUSTON MAIN
  63. Andrew L. Kocen, Maurice Brookhart, Olafs Daugulis. A highly active Ni(II)-triadamantylphosphine catalyst for ultrahigh-molecular-weight polyethylene synthesis. Nature Communications 2019, 10 (1) https://doi.org/10.1038/s41467-019-08309-8OpenURL UNIV OF HOUSTON MAIN
  64. Christopher Schwarz, Jens Handelmann, Daniel M. Baier, Alina Ouissa, Viktoria H. Gessner. Mono- and diylide-substituted phosphines (YPhos): impact of the ligand properties on the catalytic activity in gold( i )-catalysed hydroaminations. Catalysis Science & Technology 2019, 9 (23) , 6808-6815. https://doi.org/10.1039/C9CY01861AOpenURL UNIV OF HOUSTON MAIN
  65. Erfei Wang, Mao Chen. Catalyst shuttling enabled by a thermoresponsive polymeric ligand: facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium. Chemical Science 2019, 10 (36) , 8331-8337. https://doi.org/10.1039/C9SC02171JOpenURL UNIV OF HOUSTON MAIN
  66. Yiming Zhao, Matthew G. Wakeling, Fernanda Meloni, Tze Jing Sum, Huy van Nguyen, Benjamin R. Buckley, Paul W. Davies, John S. Fossey. Balancing Bulkiness in Gold(I) Phosphino-triazole Catalysis. European Journal of Organic Chemistry 2019, 2019 (31-32) , 5540-5548. https://doi.org/10.1002/ejoc.201900850OpenURL UNIV OF HOUSTON MAIN
  67. Mario Marín, Juan J. Moreno, María M. Alcaide, Eleuterio Álvarez, Joaquín López-Serrano, Jesús Campos, M. Carmen Nicasio, Ernesto Carmona. Evaluating stereoelectronic properties of bulky dialkylterphenyl phosphine ligands. Journal of Organometallic Chemistry 2019, 896 , 120-128. https://doi.org/10.1016/j.jorganchem.2019.06.003OpenURL UNIV OF HOUSTON MAIN
  68. Eva Deck, Hanna E. Wagner, Jan Paradies, Frank Breher. Redox-responsive phosphonite gold complexes in hydroamination catalysis. Chemical Communications 2019, 55 (37) , 5323-5326. https://doi.org/10.1039/C9CC01492FOpenURL UNIV OF HOUSTON MAIN
  69. Shaochen Zhang, Juan del Pozo, Filippo Romiti, Yucheng Mu, Sebastian Torker, Amir H. Hoveyda. Delayed catalyst function enables direct enantioselective conversion of nitriles to NH 2 -amines. Science 2019, 364 (6435) , 45-51. https://doi.org/10.1126/science.aaw4029OpenURL UNIV OF HOUSTON MAIN
  70. Irina P. Beletskaya, Francisco Alonso, Vladimir Tyurin. The Suzuki-Miyaura reaction after the Nobel prize. Coordination Chemistry Reviews 2019, 385 , 137-173. https://doi.org/10.1016/j.ccr.2019.01.012OpenURL UNIV OF HOUSTON MAIN
  71. Fioralba Taullaj, David Armstrong, Shaishav Datta, Alan J. Lough, Ulrich Fekl. 2-Adamantyl Complexes of Platinum. European Journal of Inorganic Chemistry 2019, 2019 (9) , 1288-1291. https://doi.org/10.1002/ejic.201900019OpenURL UNIV OF HOUSTON MAIN
  72. Philip Weber, Thorsten Scherpf, Ilja Rodstein, Dominik Lichte, Lennart T. Scharf, Lukas J. Gooßen, Viktoria H. Gessner. Ein hochaktives, Ylid‐funktionalisiertes Phosphan für die palladiumkatalysierte Aminierung von Arylchloriden. Angewandte Chemie 2019, 131 (10) , 3235-3239. https://doi.org/10.1002/ange.201810696OpenURL UNIV OF HOUSTON MAIN
  73. Philip Weber, Thorsten Scherpf, Ilja Rodstein, Dominik Lichte, Lennart T. Scharf, Lukas J. Gooßen, Viktoria H. Gessner. A Highly Active Ylide‐Functionalized Phosphine for Palladium‐Catalyzed Aminations of Aryl Chlorides. Angewandte Chemie International Edition 2019, 58 (10) , 3203-3207. https://doi.org/10.1002/anie.201810696OpenURL UNIV OF HOUSTON MAIN
  74. Jie Dong, Hui Guo, Wei Peng, Qiao-Sheng Hu. Room temperature Pd(0)/Ad3P-catalyzed coupling reactions of aryl chlorides with bis(pinacolato)diboron. Tetrahedron Letters 2019, 60 (11) , 760-763. https://doi.org/10.1016/j.tetlet.2019.01.042OpenURL UNIV OF HOUSTON MAIN
  75. Junya Arashima, Tomohiro Iwai, Masaya Sawamura. A Polystyrene‐Cross‐Linking Tricyclohexylphosphine: Synthesis, Characterization and Applications to Pd‐Catalyzed Cross‐Coupling Reactions of Aryl Chlorides. Chemistry – An Asian Journal 2019, 14 (3) , 411-415. https://doi.org/10.1002/asia.201801651OpenURL UNIV OF HOUSTON MAIN
  76. Mario Marín, Juan J. Moreno, Carlos Navarro‐Gilabert, Eleuterio Álvarez, Celia Maya, Riccardo Peloso, M. Carmen Nicasio, Ernesto Carmona. Synthesis, Structure and Nickel Carbonyl Complexes of Dialkylterphenyl Phosphines. Chemistry – A European Journal 2019, 25 (1) , 260-272. https://doi.org/10.1002/chem.201803598OpenURL UNIV OF HOUSTON MAIN
  77. Shibin Zhao, Tobias Gensch, Benjamin Murray, Zachary L. Niemeyer, Matthew S. Sigman, Mark R. Biscoe. Enantiodivergent Pd-catalyzed C–C bond formation enabled through ligand parameterization. Science 2018, 362 (6415) , 670-674. https://doi.org/10.1126/science.aat2299OpenURL UNIV OF HOUSTON MAIN
  78. . Catalytic Process Design: The Industrial Perspective. 2018,,, 31-73. https://doi.org/10.1002/9783527807253.ch2OpenURL UNIV OF HOUSTON MAIN
  79. Thorsten Scherpf, Christopher Schwarz, Lennart T. Scharf, Jana-Alina Zur, Andreas Helbig, Viktoria H. Gessner. Ylide-Functionalized Phosphines: Strong Donor Ligands for Homogeneous Catalysis. Angewandte Chemie 2018, 130 (39) , 13041-13046. https://doi.org/10.1002/ange.201805372OpenURL UNIV OF HOUSTON MAIN
  80. Thorsten Scherpf, Christopher Schwarz, Lennart T. Scharf, Jana-Alina Zur, Andreas Helbig, Viktoria H. Gessner. Ylide-Functionalized Phosphines: Strong Donor Ligands for Homogeneous Catalysis. Angewandte Chemie International Edition 2018, 57 (39) , 12859-12864. https://doi.org/10.1002/anie.201805372OpenURL UNIV OF HOUSTON MAIN
  81. Isabelle Chambrier, Luca Rocchigiani, David L. Hughes, Peter M. H. Budzelaar, Manfred Bochmann. Thermally Stable Gold(III) Alkene and Alkyne Complexes: Synthesis, Structures, and Assessment of the trans -Influence on Gold-Ligand Bond Enthalpies. Chemistry - A European Journal 2018, 24 (44) , 11467-11474. https://doi.org/10.1002/chem.201802160OpenURL UNIV OF HOUSTON MAIN
  82. David Roy, Yasuhiro Uozumi. Recent Advances in Palladium-Catalyzed Cross-Coupling Reactions at ppm to ppb Molar Catalyst Loadings. Advanced Synthesis & Catalysis 2018, 360 (4) , 602-625. https://doi.org/10.1002/adsc.201700810OpenURL UNIV OF HOUSTON MAIN
  83. Jia-Sheng Ouyang, Yan-Fang Li, Fei-Dong Huang, Dong-Dong Lu, Feng-Shou Liu. The Highly Efficient Suzuki-Miyaura Cross-Coupling of (Hetero)aryl Chlorides and (Hetero)arylboronic Acids Catalyzed by “Bulky-yet-Flexible” Palladium-PEPPSI Complexes in Air. ChemCatChem 2018, 10 (2) , 371-375. https://doi.org/10.1002/cctc.201701076OpenURL UNIV OF HOUSTON MAIN
  84. Shaoke Zhang, Helfried Neumann, Matthias Beller. Pd-Catalyzed Cyanation of (Hetero)Aryl Halides by Using Biphosphine Ligands. Chemistry - A European Journal 2018, 24 (1) , 67-70. https://doi.org/10.1002/chem.201704178OpenURL UNIV OF HOUSTON MAIN
  85. Ruixing Liu, Qiang Wang, Yin Wei, Min Shi. Synthesis of indolizine derivatives containing eight-membered rings via a gold-catalyzed two-fold hydroarylation of diynes. Chemical Communications 2018, 54 (10) , 1225-1228. https://doi.org/10.1039/C7CC09250DOpenURL UNIV OF HOUSTON MAIN
  86. Hwanjong Jang, Filippo Romiti, Sebastian Torker, Amir H. Hoveyda. Catalytic diastereo- and enantioselective additions of versatile allyl groups to N–H ketimines. Nature Chemistry 2017, 9 (12) , 1269-1275. https://doi.org/10.1038/nchem.2816OpenURL UNIV OF HOUSTON MAIN
  87. Bastien Chatelet, Paola Nava, Herve Clavier, Alexandre Martinez. Synthesis of Gold(I) Complexes Bearing Verkade's Superbases. European Journal of Inorganic Chemistry 2017, 2017 (37) , 4311-4316. https://doi.org/10.1002/ejic.201700897OpenURL UNIV OF HOUSTON MAIN
  88. Elsa Follet, Peter Mayer, David S. Stephenson, Armin R. Ofial, Guillaume Berionni. Reactivity-Tuning in Frustrated Lewis Pairs: Nucleophilicity and Lewis Basicity of Sterically Hindered Phosphines. Chemistry - A European Journal 2017, 23 (31) , 7422-7427. https://doi.org/10.1002/chem.201701080OpenURL UNIV OF HOUSTON MAIN
  89. Paul Mehlmann, Christian Mück-Lichtenfeld, Tristan T. Y. Tan, Fabian Dielmann. Tris(imidazolin-2-ylidenamino)phosphine: A Crystalline Phosphorus(III) Superbase That Splits Carbon Dioxide. Chemistry - A European Journal 2017, 23 (25) , 5929-5933. https://doi.org/10.1002/chem.201604971OpenURL UNIV OF HOUSTON MAIN
  90. David Armstrong, Fioralba Taullaj, Kamalpreet Singh, Bijan Mirabi, Alan J. Lough, Ulrich Fekl. Adamantyl metal complexes: new routes to adamantyl anions and new transmetallations. Dalton Transactions 2017, 46 (19) , 6212-6217. https://doi.org/10.1039/C7DT00428AOpenURL UNIV OF HOUSTON MAIN
  91. Meng-Qi Yan, Jia Yuan, Fang Lan, Si-Hao Zeng, Meng-Yue Gao, Sheng-Hua Liu, Jian Chen, Guang-Ao Yu. An active catalytic system for Suzuki–Miyaura cross-coupling reactions using low levels of palladium loading. Org. Biomol. Chem. 2017, 15 (18) , 3924-3929. https://doi.org/10.1039/C7OB00178AOpenURL UNIV OF HOUSTON MAIN

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE