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Synthesis 2015; 47(24): 3891-3900
DOI: 10.1055/s-0035-1560260
DOI: 10.1055/s-0035-1560260
paper
Visible-Light-Induced Photocatalysis of 1,1,1-Trifluoro-2-iodoethane with Alkylalkenes and Silyl Enol Ethers
Further Information
Publication History
Received: 22 July 2015
Accepted after revision: 21 August 2015
Publication Date:
16 September 2015 (online)
Abstract
Reactions of 1,1,1-trifluoro-2-iodoethane with alkylalkenes and silyl enol ethers were performed in the presence of a catalytic amount of fac-Ir(ppy)3 and an excessive amount of Hünig’s base in acetonitrile irradiated by a 24 W fluorescent lamp under nitrogen atmosphere for 48 hours. The visible-light-induced photoredox reactions introduce simultaneously a 2,2,2-trifluoroethyl group and an iodine atom to both sides of the double bond of ordinary alkenes via an atom-transfer radical addition (ATRA). The same reaction with silyl enol ethers generates β-trifluoromethyl ketones, which are typically a challenge to synthesize. The reactions proved to be tolerant of a variety of functionalities.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560260.
- Supporting Information
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