Literature DB >> 16774239

Rhodium-catalyzed addition of arylboronic acids to isatins: an entry to diversity in 3-aryl-3-hydroxyoxindoles.

Patrick Y Toullec1, Richard B C Jagt, Johannes G de Vries, Ben L Feringa, Adriaan J Minnaard.   

Abstract

[reaction: see text] A general method for the catalytic 1,2-addition of aryl and alkenyl boronic acids to isatins is described using a rhodium(I)/triphenylphosphite catalyst. The application of this transformation allows the synthesis of a variety of 3-aryl-3-hydroxyoxindole building blocks in high yields. An enantioselective version of this reaction using a rhodium(I)/phosphoramidite system is also presented.

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Year:  2006        PMID： 16774239     DOI： 10.1021/ol0608101

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


  8 in total

1.  Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones.

Authors:  Yuan-Xi Liao; Chun-Hui Xing; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2012-03-01       Impact factor: 6.005

2.  Anionic four-electron donor-based palladacycles as catalysts for addition reactions of arylboronic acids with alpha,beta-unsaturated ketones, aldehydes, and alpha-ketoesters.

Authors:  Ping He; Yong Lu; Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

3.  Highly enantioselective catalytic benzoyloxylation of 3-aryloxindoles using chiral VAPOL calcium phosphate.

Authors:  Zuhui Zhang; Wenhua Zheng; Jon C Antilla
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-22       Impact factor: 15.336

4.  Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans.

Authors:  Jingqi Wang; Erika A Crane; Karl A Scheidt
Journal:  Org Lett       Date:  2011-05-18       Impact factor: 6.005

5.  A concise silylamine approach to 2-amino-3-hydroxy-indoles with potent in vivo antimalaria activity.

Authors:  Sameer Urgaonkar; Joseph F Cortese; Robert H Barker; Mandy Cromwell; Adelfa E Serrano; Dyann F Wirth; Jon Clardy; Ralph Mazitschek
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

6.  Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via P-Chiral Monophosphorous Ligands.

Authors:  Rui Miao; Yanping Xia; Yifei Wei; Lu Ouyang; Renshi Luo
Journal:  Molecules       Date:  2022-06-17       Impact factor: 4.927

7.  Enantioselective allylation, crotylation, and reverse prenylation of substituted isatins: iridium-catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Junji Itoh; Soo Bong Han; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Phosphinite- and phosphite-based Type I palladacycles as highly active catalysts for addition reactions of arylboronic acids with aldehydes, α,β-unsaturated ketones, α-ketoesters, and aldimines.

Authors:  Ping He; Yong Lu; Qiao-Sheng Hu
Journal:  Tetrahedron Lett       Date:  2007-07-23       Impact factor: 2.415
  8 in total

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