Literature DB >> 16131169

Room temperature hydroalkylation of electron-deficient olefins: sp3 C-H functionalization via a lewis acid-catalyzed intramolecular redox event.

Stefan J Pastine1, Kevin M McQuaid, Dalibor Sames.   

Abstract

A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.

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Year:  2005        PMID： 16131169     DOI： 10.1021/ja053337f

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


  18 in total

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Journal:  J Am Chem Soc       Date:  2011-03-07       Impact factor: 15.419

6.  Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

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7.  C-H bond functionalization via hydride transfer: Lewis acid catalyzed alkylation reactions by direct intramolecular coupling of sp3 C-H bonds and reactive alkenyl oxocarbenium intermediates.

Authors:  Kevin M McQuaid; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

8.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level using allyl acetate as an allyl metal surrogate.

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9.  C-H bond functionalization via hydride transfer: direct coupling of unactivated alkynes and sp(3) C-H bonds catalyzed by platinum tetraiodide.

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