Literature DB >> 14518981

Synthesis of substituted oxindoles from alpha-chloroacetanilides via palladium-catalyzed C[bond]H functionalization.

Edward J Hennessy1, Stephen L Buchwald.   

Abstract

A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, alpha-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed.

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Year:  2003        PMID: 14518981     DOI: 10.1021/ja037546g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  22 in total

1.  Total synthesis of (±)-cycloclavine and (±)-5-epi-cycloclavine.

Authors:  Filip R Petronijevic; Peter Wipf
Journal:  J Am Chem Soc       Date:  2011-04-28       Impact factor: 15.419

2.  Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors:  Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal:  Synthesis (Stuttg)       Date:  2012-05-25       Impact factor: 3.157

3.  Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

Authors:  Jianming Lu; Xianghui Tan; Chuo Chen
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

4.  Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway.

Authors:  Natalia Chernyak; Serge I Gorelsky; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-07       Impact factor: 15.336

Review 5.  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

6.  Palladium-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

Authors:  Alexander R O Venning; Patrick T Bohan; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2015-03-16       Impact factor: 15.419

7.  Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation.

Authors:  Raissa M Trend; Yeeman K Ramtohul; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

8.  Nickel-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

Authors:  Quentin D Tercenio; Erik J Alexanian
Journal:  Tetrahedron       Date:  2019-05-25       Impact factor: 2.457

9.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

10.  Insights into directing group ability in palladium-catalyzed C-H bond functionalization.

Authors:  Lopa V Desai; Kara J Stowers; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2008-09-10       Impact factor: 15.419

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