Literature DB >> 19296693

Selective monoarylation of acetate esters and aryl methyl ketones using aryl chlorides.

Mark R Biscoe1, Stephen L Buchwald.   

Abstract

Simple, efficient procedures for the monoarylation of acetate esters and n class="Chemical">aryl methyl ketones using aryl chlorides are presented. Previously, no general method was available to ensure the highly selective monoarylation of these classes of substrates using aryl chlorides. Using palladium precatalysts recently reported by our group, these reactions are easily accomplished under mild conditions that tolerate a wide array of heterocyclic substrates.

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Year:  2009        PMID: 19296693      PMCID: PMC2747740          DOI: 10.1021/ol900295u

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  17 in total

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Authors:  S Lee; N A Beare; J F Hartwig
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2.  Catalytic asymmetric vinylation of ketone enolates.

Authors:  A Chieffi; K Kamikawa; J Ahman; J M Fox; S L Buchwald
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3.  An improved catalyst for the asymmetric arylation of ketone enolates.

Authors:  Takayuki Hamada; André Chieffi; Jens Ahman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-02-20       Impact factor: 15.419

4.  Suzuki-Miyaura, alpha-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex.

Authors:  Oscar Navarro; Nicolas Marion; Yoshihiro Oonishi; Roy A Kelly; Steven P Nolan
Journal:  J Org Chem       Date:  2006-01-20       Impact factor: 4.354

5.  Synthesis, characterization, and catalytic activity of N-heterocyclic carbene (NHC) palladacycle complexes.

Authors:  Mihai S Viciu; Roy A Kelly; Edwin D Stevens; Frédéric Naud; Martin Studer; Steven P Nolan
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

6.  Alpha-arylation of esters catalyzed by the Pd(I) dimer {[P(t-Bu)3]PdBr}2.

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

7.  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

8.  Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.

Authors:  Xuebin Liao; Zhiqiang Weng; John F Hartwig
Journal:  J Am Chem Soc       Date:  2007-12-13       Impact factor: 15.419

9.  Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles.

Authors:  Darcy A Culkin; John F Hartwig
Journal:  Acc Chem Res       Date:  2003-04       Impact factor: 22.384

10.  Palladium-catalyzed alpha-vinylation of carbonyl compounds.

Authors:  Jinkun Huang; Emilio Bunel; Margaret M Faul
Journal:  Org Lett       Date:  2007-09-22       Impact factor: 6.005

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Review 2.  Stable cyclic carbenes and related species beyond diaminocarbenes.

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Journal:  J Org Chem       Date:  2013-08-13       Impact factor: 4.354

4.  Palladium-catalyzed α-arylation of zinc enolates of esters: reaction conditions and substrate scope.

Authors:  Takuo Hama; Shaozhong Ge; John F Hartwig
Journal:  J Org Chem       Date:  2013-08-21       Impact factor: 4.354

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

Authors:  Gary A Molander; Kaitlin M Traister; Thiago Barcellos
Journal:  J Org Chem       Date:  2013-04-09       Impact factor: 4.354

6.  Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.

Authors:  Enrico Marelli; Martin Corpet; Yury Minenkov; Rifahath M Neyyappadath; Alessandro Bismuto; Giulia Buccolini; Massimiliano Curcio; Luigi Cavallo; Steven P Nolan
Journal:  ACS Catal       Date:  2016-03-30       Impact factor: 13.084

  6 in total

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