Literature DB >> 18321119

Palladium-catalyzed alpha-arylation of oxindoles.

Matthew J Durbin1, Michael C Willis.   

Abstract

A catalyst generated from Pd(dba)2 and the bulky electron-rich phosphine ligand 2-(dicyclohexylphosphino)-2',4', 6'-tri-i-propyl-1-1'-biphenyl is effective for the alpha-arylation of oxindoles. Generation of the potassium-enolates of a range of oxindoles allows coupling with aryl chlorides, bromides, and triflates. Significant variation of the substitution pattern on both the oxindole and aryl halide is possible.

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Year:  2008        PMID： 18321119     DOI： 10.1021/ol800141t

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


  11 in total

1.  Alpha-arylation of 3-aryloxindoles.

Authors:  Cheng-Kang Mai; Matthew F Sammons; Tarek Sammakia
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

2.  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

3.  Tandem C(sp3)-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones.

Authors:  Jacqueline Jiménez; Byeong-Seon Kim; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2016-08-02       Impact factor: 5.837

4.  Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile.

Authors:  Kyle W Quasdorf; Alexander D Huters; Michael W Lodewyk; Dean J Tantillo; Neil K Garg
Journal:  J Am Chem Soc       Date:  2012-01-11       Impact factor: 15.419

5.  A concise formal synthesis of diazonamide A by the stereoselective construction of the C10 quaternary center.

Authors:  Cheng-Kang Mai; Matthew F Sammons; Tarek Sammakia
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-22       Impact factor: 15.336

6.  Rotational isomers of N-methyl-N-arylacetamides and their derived enolates: implications for asymmetric Hartwig oxindole cyclizations.

Authors:  Jérémie Mandel; Xiaohong Pan; E Ben Hay; Steven J Geib; Craig S Wilcox; Dennis P Curran
Journal:  J Org Chem       Date:  2013-04-09       Impact factor: 4.354

7.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

8.  Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles.

Authors:  Ryan A Altman; Alan M Hyde; Xiaohua Huang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2008-06-28       Impact factor: 15.419

9.  Palladium-catalyzed direct C(sp3)-H arylation of indole-3-ones with aryl halides: a novel and efficient method for the synthesis of nucleophilic 2-monoarylated indole-3-ones.

Authors:  Yong-Long Zhao; Yong-Qin Tang; Xing-Hai Fei; Tao Xiao; Ya-Dong Lu; Xiao-Zhong Fu; Bin He; Meng Zhou; Chun Li; Peng-Fei Xu; Yuan-Yong Yang
Journal:  RSC Adv       Date:  2018-07-16       Impact factor: 3.361

Review 10.  α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds.

Authors:  Mei Wang; Wei Wang; Dashan Li; Wen-Jing Wang; Rui Zhan; Li-Dong Shao
Journal:  Nat Prod Bioprospect       Date:  2021-06-07
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