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

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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… Click to show full 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.

Keywords: methylation; methylation alkynylation; methyl source; peroxide; dicumyl peroxide; peroxide methyl

Journal Title: Synthesis
Year Published: 2021

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