Literature DB >> 11841272

A highly active Suzuki catalyst for the synthesis of sterically hindered biaryls: novel ligand coordination.

Jingjun Yin1, Matthew P Rainka, Xiao-Xiang Zhang, Stephen L Buchwald.   

Abstract

A catalyst system for the preparation of biaryls containing four ortho substituents via Suzuki coupling is described. The combination of a catalytic quantity of Pd2(dba)3 with either an electron-rich biarylphosphine or DPEPhos is effective using a wide range of substrates. The X-ray crystal structure of (dba)Pd(2-(9-phenanthryl)phenyl-dicyclohexylphosphine), in which the Pd is coordinated to the 9,10-double bond of the phenanthryl group, is also reported.

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Year:  2002        PMID: 11841272     DOI: 10.1021/ja017082r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  16 in total

1.  DFT Investigation of Suzuki-Miyaura Reactions with Aryl Sulfamates Using a Dialkylbiarylphosphine-Ligated Palladium Catalyst.

Authors:  Patrick R Melvin; Ainara Nova; David Balcells; Nilay Hazari; Mats Tilset
Journal:  Organometallics       Date:  2017-09-13       Impact factor: 3.876

2.  Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates.

Authors:  Gary A Molander; Steven R Wisniewski
Journal:  J Am Chem Soc       Date:  2012-10-01       Impact factor: 15.419

3.  Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction.

Authors:  Joshua E Ney; John P Wolfe
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

4.  Synthesis of an electron-rich KITPHOS monophosphine, preparation of derived metal complexes and applications in catalysis.

Authors:  Simon Doherty; Catherine H Smyth; Julian G Knight; Stephen A K Hashmi
Journal:  Nat Protoc       Date:  2012-09-20       Impact factor: 13.491

Review 5.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis.

Authors:  Nitinchandra Dahyabhai Patel; Joshua D Sieber; Sergei Tcyrulnikov; Bryan J Simmons; Daniel Rivalti; Krishnaja Duvvuri; Yongda Zhang; Donghong A Gao; Keith R Fandrick; Nizar Haddad; Kendricks So Lao; Hari Prasad Reddy Mangunuru; Soumik Biswas; Bo Qu; Nelu Grinberg; Scott Pennino; Heewon Lee; Jinhua J Song; B Frank Gupton; Neil K Garg; Marisa C Kozlowski; Chris H Senanayake
Journal:  ACS Catal       Date:  2018-09-20       Impact factor: 13.084

7.  Palladium-oxygen and palladium-arene interactions in complexes derived from biaryl aminocarbenes: comparison with biaryl phosphanes.

Authors:  Joan Vignolle; Heinz Gornitzka; Bruno Donnadieu; Didier Bourissou; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands.

Authors:  Ruben Martin; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

9.  Palladium-catalyzed chemoselective allylic substitution, Suzuki-Miyaura cross-coupling, and allene formation of bifunctional 2-B(pin)-substituted allylic acetate derivatives.

Authors:  Byeong-Seon Kim; Mahmud M Hussain; Nusrah Hussain; Patrick J Walsh
Journal:  Chemistry       Date:  2014-07-30       Impact factor: 5.236

10.  Intramolecular Arene C-H to C-P Functionalization Mediated by Ni(II) and Pd(II).

Authors:  Sandy Suseno; Theodor Agapie
Journal:  Organometallics       Date:  2013-06-10       Impact factor: 3.876

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