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Synthesis 2021; 53(24): 4700-4708
DOI: 10.1055/a-1528-8357
DOI: 10.1055/a-1528-8357
paper
Methylation Alkynylation of Terminal Alkenes via 1,2-Alkynyl Migration Using Dicumyl Peroxide as the Methyl Source
Authors
We are grateful for financial support from the National Natural Science Foundation of China (No. 21502049 and 51573040) and the Natural Science Foundation of Hunan Province (No. 2018JJ2032).
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1528-8357.
- Supporting Information (PDF)
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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For cyano migration, see:
For heteroaryl migration, see:
For radical-mediated difunctionalization of alkenes, see:
For other types of difunctionalization of alkenes, see:
For reviews, see:
For recent examples, see:
For methylation using peroxides as the methyl source, see: