Cobalt-Tertiary Amine Mediated Peroxy-trifluoromethylation and -halodifluoromethylation of Alkenes with CF2XBr (X = F, Cl, Br) and tert-Butyl Hydroperoxide

An efficient cobalt-tertiary amine mediated peroxy-trifluoromethylation and -halodifluoromethylation of alkenes with simple and inexpensive CF2XBr (X = F, CI, Br) has been described. This method demonstrated broad substrate scope and good to high yields with the tolerance of mono-, di-, and trisubst...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 54; no. 9; pp. 2193 - 2204
Main Authors Pang, Liangzhi, Sun, Qilin, Huang, Zhan, Li, Suhua, Li, Qiankun
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.05.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DESIGN
ARENES
DECOMPOSITION
CATALYZED CARBONYLATION-PEROXIDATION
cobalt
BROMODIFLUOROMETHYLATION
peroxyl
FLUORINE
BROMOTRIFLUOROMETHANE
trifluoromethylation
GEM-DIFLUOROALLYLATION
bromo-difluoromethylation
DERIVATIVES
DIFUNCTIONALIZATIONS
chlorodifluoromethylation
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Summary:An efficient cobalt-tertiary amine mediated peroxy-trifluoromethylation and -halodifluoromethylation of alkenes with simple and inexpensive CF2XBr (X = F, CI, Br) has been described. This method demonstrated broad substrate scope and good to high yields with the tolerance of mono-, di-, and trisubstituted alkenes with both electron-donating and electron-withdrawing groups. The protocol provides an efficient access to various beta-peroxyl trifluoromethyl/halodifluoromethyl derivatives. Further transformation of these type of compounds into other useful molecules, such as a ketene aminal, an alpha-trifluoromethyl ketone, and a gem-difluoroalkene, demonstrated the utility of this methodology.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1702-4445