Carbon–Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)–CF3 Bond Cleavage

Autor:	Renhua Qiu, Nobuaki Kambe, Liyuan Le, Longzhi Zhu, Mingpan Yan, Chak-Tong Au
Rok vydání:	2019
Předmět:	chemistry.chemical_classification 010405 organic chemistry Aryl Organic Chemistry 010402 general chemistry 01 natural sciences Isocyanate Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Carbon–carbon bond Reagent Amide Alkoxide Bond cleavage Alkyl
Zdroj:	The Journal of Organic Chemistry. 84:5635-5644
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.9b00583
Popis:	The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF3 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c718c4208ce20fa6f4ac8fcfe6763552 https://doi.org/10.1021/acs.joc.9b00583 Zobrazit plný text záznamu