Carbon-Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)-CF 3 Bond Cleavage

The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily avai...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-05, Vol.84 (9), p.5635-5644
Main Authors: Zhu, Longzhi, Le, Liyuan, Yan, Mingpan, Au, Chak-Tong, Qiu, Renhua, Kambe, Nobuaki
Format: Article
Language:English
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Summary:The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates. The control experiments show that the reaction proceeds via an isocyanate intermediate and/or alkoxide/amide dual anionic intermediate.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00583