Literature DB >> 15469301

An extremely active catalyst for the Negishi cross-coupling reaction.

Jacqueline E Milne1, Stephen L Buchwald.   

Abstract

A new catalyst system for the Pd-catalyzed cross-coupling of organozinc reagents with aryl halides (Negishi coupling) has been developed. This system permits efficient preparation of hindered biaryls (tri- and tetra-ortho-substituted), functions effectively at low levels of catalyst, and tolerates a wide range of functional groups and heterocyclic substrates. A systematic study of ligand structure was performed and was correlated with catalyst activity.

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Year:  2004        PMID: 15469301     DOI: 10.1021/ja0474493

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


  40 in total

1.  Why You Really Should Consider Using Palladium-Catalyzed Cross-Coupling of Silanols and Silanolates.

Authors:  Scott E Denmark; Andrea Ambrosi
Journal:  Org Process Res Dev       Date:  2015       Impact factor: 3.317

2.  Structural, Mechanistic, Spectroscopic, and Preparative Studies on the Lewis Base Catalyzed, Enantioselective Sulfenofunctionalization of Alkenes.

Authors:  Eduard Hartmann; Scott E Denmark
Journal:  Helv Chim Acta       Date:  2017-09-14       Impact factor: 2.164

3.  Synthesis of 5-fluoroalkylated pyrimidine nucleosides via Negishi cross-coupling.

Authors:  Ann-Marie Chacko; Wenchao Qu; Hank F Kung
Journal:  J Org Chem       Date:  2008-06-04       Impact factor: 4.354

4.  Preparation of 2,3-Disubstituted Indoles by Sequential Larock Heteroannulation and Silicon-Based Cross-Coupling Reactions.

Authors:  Scott E Denmark; John D Baird
Journal:  Tetrahedron       Date:  2009-04-18       Impact factor: 2.457

Review 5.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

6.  Synthesis of hindered biphenyls by sequential non-transition metal-catalyzed reaction/palladium-catalyzed cross-couplings.

Authors:  Ping He; Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Tetrahedron Lett       Date:  2008-03-17       Impact factor: 2.415

7.  Nine-step enantioselective total synthesis of (-)-vincorine.

Authors:  Benjamin D Horning; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-04-19       Impact factor: 15.419

Review 8.  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

9.  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

10.  Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.

Authors:  Chong Han; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

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