4.8 Article

Copper-Catalyzed Silylperoxidation Reaction of α,β-Unsaturated Ketones, Esters, Amides, and Conjugated Enynes

Journal

ACS CATALYSIS
Volume 7, Issue 10, Pages 7120-7125

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b02754

Keywords

silylation; peroxidation; alkenes; radicals; silanes

Funding

  1. National Natural Science Foundation of China [21672198]
  2. State Key Program of National Natural Science Foundation of China [21432009]
  3. State Key Laboratory of Elemento-organic Chemistry Nankai University [201620]
  4. Open Project of Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University [2017110]

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A synthetic method of copper-catalyzed silylperoxidation of alpha,beta-unsaturated carbonyl compounds and conjugated enynes has been developed. The realization of silylperoxidation of the carbon carbon double bond permits direct access to silicon-containing peroxy products in moderate to good yields. Furthermore, this protocol distinguishes itself by operational simplicity and exhibiting good tolerance of a wide scope of functional groups. This strategy provides an efficient approach to the 1,2-difunctionalization of alpha,beta-unsaturated carbonyl compounds and conjugated enynes.

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