Literature DB >> 18540631

Direct arylation of oxazoles at C2. A concise approach to consecutively linked oxazoles.

Emmanuel Ferrer Flegeau1, Matthew E Popkin, Michael F Greaney.   

Abstract

The synthesis of bis- and trisoxazoles via direct arylation is discussed. A variety of aryl groups can be installed at the 2-position of 5-aryl and 5-carboxy-substituted oxazoles under mild conditions using palladium catalysis on water. The direct arylation method can be extended to the synthesis of bis- and trisoxazoles if 2-triisopropylsilyl-4-iodooxazole is used as the electrophile in the arylation.

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Year:  2008        PMID: 18540631     DOI: 10.1021/ol800869g

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


  12 in total

1.  Methodology for the Synthesis of Substituted 1,3-Oxazoles.

Authors:  David R Williams; Liangfeng Fu
Journal:  Synlett       Date:  2009-12-22       Impact factor: 2.454

2.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

3.  Room temperature C-H activation and cross-coupling of aryl ureas in water.

Authors:  Takashi Nishikata; Alexander R Abela; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

4.  Efficient Suzuki and Stille Reactions for Regioselective Strategies of Incorporation of the 1,3-Oxazole Heterocycle. Mild Desulfonylation for the Synthesis of C-4 and C-5 Monosubstituted Oxazoles.

Authors:  David R Williams; Liangfeng Fu
Journal:  Synlett       Date:  2010-07-01       Impact factor: 2.454

5.  General methodology for the preparation of 2,5-disubstituted-1,3-oxazoles.

Authors:  David R Williams; Liangfeng Fu
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

6.  Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  J Org Chem       Date:  2012-08-13       Impact factor: 4.354

7.  Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides.

Authors:  Feng Gao; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chem Commun (Camb)       Date:  2014-07-31       Impact factor: 6.222

8.  Palladium- and copper-catalyzed arylation of carbon-hydrogen bonds.

Authors:  Olafs Daugulis; Hien-Quang Do; Dmitry Shabashov
Journal:  Acc Chem Res       Date:  2009-08-18       Impact factor: 22.384

9.  Recent advances in direct C-H arylation: Methodology, selectivity and mechanism in oxazole series.

Authors:  Cécile Verrier; Pierrik Lassalas; Laure Théveau; Guy Quéguiner; François Trécourt; Francis Marsais; Christophe Hoarau
Journal:  Beilstein J Org Chem       Date:  2011-11-29       Impact factor: 2.883

10.  Cationic Pd(II)-catalyzed C-H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies.

Authors:  Takashi Nishikata; Alexander R Abela; Shenlin Huang; Bruce H Lipshutz
Journal:  Beilstein J Org Chem       Date:  2016-05-20       Impact factor: 2.883

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