Synthesis of beta-Trifluoromethylated Ketones from Propargylic Alcohols by Visible Light Photoredox Catalysis

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초록

Regioselective trifluoromethylation at a remote position represents an important challenge in the development of biologically active molecules and functional materials. A practical method to access -trifluoromethyl ketones from readily available propargylic alcohols by visible light photocatalysis has been developed. Trifluoromethylation of propargylic alcohols with CF3I in the presence of Ru(bpy)(3)Cl-2 as the photocatalyst followed by double-bond migration/keto-enol tautomerization provides -trifluoromethyl ketones as the final product.

키워드

Photocatalysis; Radical reactions; Trifluoromethylation; Propargylic alcohols; Ketones; SILYL ENOL ETHERS; RADICAL TRIFLUOROMETHYLATION; ALLYLIC ALCOHOLS; REGIOSELECTIVE 1,4-TRIFLUOROMETHYLATION; NUCLEOPHILIC TRIFLUOROMETHYLATION; SUBSTITUTED KETONES; FACILE SYNTHESIS; ATE ENOLATE; ALPHA; ALKENES
제목
Synthesis of beta-Trifluoromethylated Ketones from Propargylic Alcohols by Visible Light Photoredox Catalysis
저자
Park, Sehyun; Joo, Jung Min; Cho, Eun Jin
DOI
10.1002/ejoc.201500031
발행일
2015-07
유형
Article
저널명
European Journal of Organic Chemistry
권
2015
호
19
페이지
4093 ~ 4097