Literature DB >> 23172689

Mild and general conditions for negishi cross-coupling enabled by the use of palladacycle precatalysts.

Yang Yang1, Nathan J Oldenhuis, Stephen L Buchwald.   

Abstract

A wide range of biaryls were synthesized by palladium-catalyzed Negishi cross-couplings at ambient temperature or with low catalyst loading. This protocol features the use of a recently reported aminobiphenyl palladacycle precatalyst to generate the catalytically active XPhosPd(0) species. Significantly, a wide range of challenging heterocyclic and polyfluorinated aromatic substrates can be employed to give products in excellent yields.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 23172689      PMCID： PMC3697109          DOI： 10.1002/anie.201207750

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  34 in total

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

Authors:  Jacqueline E Milne; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

2.  Pd-PEPPSI-IPent: low-temperature negishi cross-coupling for the preparation of highly functionalized, tetra-ortho-substituted biaryls.

Authors:  Selçuk Calimsiz; Mahmoud Sayah; Debasis Mallik; Michael G Organ
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-08       Impact factor: 15.336

3.  The development of bulky palladium NHC complexes for the most-challenging cross-coupling reactions.

Authors:  Cory Valente; Selçuk Calimsiz; Ka Hou Hoi; Debasis Mallik; Mahmoud Sayah; Michael G Organ
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336

Review 4.  Selected patented cross-coupling reaction technologies.

Authors:  Jean-Pierre Corbet; Gérard Mignani
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

5.  A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

Review 6.  Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

Authors:  Javier Magano; Joshua R Dunetz
Journal:  Chem Rev       Date:  2011-03-09       Impact factor: 60.622

7.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

8.  Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand.

Authors:  Yuki Nakamura; Naohiko Yoshikai; Laurean Ilies; Eiichi Nakamura
Journal:  Org Lett       Date:  2012-06-12       Impact factor: 6.005

9.  Palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands.

Authors:  David X Yang; Steven L Colletti; Kevin Wu; Maoying Song; George Y Li; Hong C Shen
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

10.  A general solution for the 2-pyridyl problem.

Authors:  Graham R Dick; Eric M Woerly; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336
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  19 in total

1.  A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

Authors:  Bing Zheng; Tiezheng Jia; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-01-13       Impact factor: 5.837

2.  Storable N-phenylcarbamate palladacycles for rapid functionalization of an alkyne-encoded protein.

Authors:  Gang Cheng; Reyna K V Lim; Carlo P Ramil; Qing Lin
Journal:  Chem Commun (Camb)       Date:  2014-10-11       Impact factor: 6.222

3.  Palladium-catalyzed completely linear-selective Negishi cross-coupling of allylzinc halides with aryl and vinyl electrophiles.

Authors:  Yang Yang; Thomas J L Mustard; Paul Ha-Yeon Cheong; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-08       Impact factor: 15.336

4.  Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands.

Authors:  Bryan T Ingoglia; Stephen L Buchwald
Journal:  Org Lett       Date:  2017-05-12       Impact factor: 6.005

5.  Mild and general palladium-catalyzed synthesis of methyl aryl ethers enabled by the use of a palladacycle precatalyst.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-07-24       Impact factor: 6.005

6.  Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles: substrate scope and mechanistic investigation.

Authors:  M Alexander Düfert; Kelvin L Billingsley; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-08-16       Impact factor: 15.419

7.  Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions.

Authors:  James R Colombe; Sebastian Bernhardt; Christos Stathakis; Stephen L Buchwald; Paul Knochel
Journal:  Org Lett       Date:  2013-10-24       Impact factor: 6.005

8.  A Neophyl Palladacycle as an Air- and Thermally Stable Precursor to Oxidative Addition Complexes.

Authors:  Ryan P King; Shane W Krska; Stephen L Buchwald
Journal:  Org Lett       Date:  2021-10-06       Impact factor: 6.072

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.  Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts.

Authors:  Chi Wai Cheung; David S Surry; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-07-01       Impact factor: 6.005
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