Methylation Alkynylation of Terminal Alkenes via 1,2-Alkynyl Migration Using Dicumyl Peroxide as the Methyl Source

Abstract

The metal-free oxidative alkene methylation/alkynylation of 1,4-enyn-3-ols with an organic peroxide as the methyl source has been developed, which provides straightforward and practical access to the challenging quaternary-carbon-containing but-3-yn-1-ones. The method is reasoned to go through methylation of functional alkenes utilizing dicumyl peroxide as the methylating reagent and subsequent intermolecular cyclization/1,2-alkynyl migration. This reaction has an excellent functional group tolerance, broad substrate scope, and exquisite selectivity.

Key words

alkene difunctionalization - migration reaction - radical

Publication History

Received: 08 May 2021

Accepted after revision: 15 June 2021

Accepted Manuscript online:
15 June 2021

Article published online:
23 August 2021

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