Cobalt(III)-Catalyzed and DMSO-Involved Allylation of 1,3-Dicarbonyl Compounds with Alkenes

Xuefeng Xu; Yue Shi; Di Wang; Yanhua Ding; Shuyang Chen; Xu Zhang

doi:10.1021/acs.joc.2c01796

Cobalt(III)-Catalyzed and DMSO-Involved Allylation of 1,3-Dicarbonyl Compounds with Alkenes

J Org Chem. 2022 Nov 4;87(21):14352-14363. doi: 10.1021/acs.joc.2c01796. Epub 2022 Oct 20.

Authors

Xuefeng Xu¹, Yue Shi¹, Di Wang¹, Yanhua Ding¹, Shuyang Chen¹, Xu Zhang¹

Affiliation

¹ Engineering Technology Research Center of Henan Province for Solar Catalysis, College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang 473061, China.

PMID: 36263891
DOI: 10.1021/acs.joc.2c01796

Abstract

Cobalt(III)-catalyzed allylation of 1,3-dicarbonyl compounds has been reported with in situ generated allyl reagents from alkenes and dimethyl sulfoxide (DMSO). This novel protocol enables a high regio- and stereoselective access for a broad range of allyl 1,3-dicarbonyl compounds. In the transformation, DMSO plays the role of a C1 source, and it incorporates with alkenes to form the allyl reagent allylic methyl thioether. Moreover, a multiple-step pathway has been proposed to rationalize the mechanism study, which involves silver-mediated coupling, Co(III)-catalyzed π-allylation, and intermolecular nucleophilic substitution.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes*
Allyl Compounds*
Catalysis
Cobalt
Dimethyl Sulfoxide
Indicators and Reagents
Stereoisomerism

Substances

Alkenes
Dimethyl Sulfoxide
Allyl Compounds
Cobalt
Indicators and Reagents