Literature DB >> 23570264

Palladium-catalyzed α-arylation of 2-chloroacetates and 2-chloroacetamides.

Gary A Molander1, Kaitlin M Traister, Thiago Barcellos.   

Abstract

A method has been developed for the Pd-catalyzed synthesis of α-(hetero)aryl esters and amides through a Suzuki-Miyaura cross-coupling reaction. This method avoids the use of strong base, does not necessitate inert or low temperature formation of reagents, and does not require the use of a large excess of organometallic reagent. Utilization of organotrifluoroborate salts as nucleophilic partners allows a variety of functional groups and heterocyclic compounds to be tolerated.

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Year:  2013        PMID: 23570264      PMCID: PMC3668638          DOI: 10.1021/jo400488q

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  26 in total

1.  Palladium-catalyzed alpha-arylation of esters: ideal new methodology for discovery chemistry.

Authors:  Guy C Lloyd-Jones
Journal:  Angew Chem Int Ed Engl       Date:  2002-03-15       Impact factor: 15.336

Review 2.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

3.  Palladium-catalyzed cross-coupling of sterically demanding boronic acids with α-bromocarbonyl compounds.

Authors:  Bettina Zimmermann; Wojciech I Dzik; Thomas Himmler; Lukas J Goossen
Journal:  J Org Chem       Date:  2011-09-13       Impact factor: 4.354

4.  Direct use of dioxygen as an oxygen source: catalytic oxidative synthesis of amides.

Authors:  Wei Wei; Xiao-Yu Hu; Xiao-Wei Yan; Qiang Zhang; Ming Cheng; Jian-Xin Ji
Journal:  Chem Commun (Camb)       Date:  2011-11-17       Impact factor: 6.222

5.  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

6.  Organotrifluoroborate hydrolysis: boronic acid release mechanism and an acid-base paradox in cross-coupling.

Authors:  Alastair J J Lennox; Guy C Lloyd-Jones
Journal:  J Am Chem Soc       Date:  2012-04-19       Impact factor: 15.419

7.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       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.  Palladium-catalyzed alpha-arylation of esters with chloroarenes.

Authors:  Takuo Hama; John F Hartwig
Journal:  Org Lett       Date:  2008-03-22       Impact factor: 6.005

10.  Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides.

Authors:  Fabio Bellina; Renzo Rossi
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

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  3 in total

Review 1.  The Fascinating Chemistry of α-Haloamides.

Authors:  Anna Fantinati; Vinicio Zanirato; Paolo Marchetti; Claudio Trapella
Journal:  ChemistryOpen       Date:  2020-01-13       Impact factor: 2.911

2.  Pd-catalyzed alkynylation of 2-chloroacetates and 2-chloroacetamides with potassium alkynyltrifluoroborates.

Authors:  Gary A Molander; Kaitlin M Traister
Journal:  Org Lett       Date:  2013-09-16       Impact factor: 6.005

3.  Carbonylative Suzuki couplings of aryl bromides with boronic acid derivatives under base-free conditions.

Authors:  Klaus M Bjerglund; Troels Skrydstrup; Gary A Molander
Journal:  Org Lett       Date:  2014-03-17       Impact factor: 6.005

  3 in total

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