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Dual Roles of tert ‐Butyl Nitrite in the Transition Metal‐ and External Oxidant‐Free Trifluoromethyloximation of Alkenes
Author(s) -
Wu Ya,
Zhang Yanli,
Yang Zhen,
Jiao Jingchao,
Zheng Xiaoke,
Feng Weisheng,
Zhang Mengsha,
Cheng Hao,
Tang Lin
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201901856
Subject(s) - chemistry , regioselectivity , reagent , nitrite , transition metal , combinatorial chemistry , trifluoromethyl , nitro , organic chemistry , catalysis , alkyl , nitrate
Abstract By employing tert ‐butyl nitrite as both nitrogen source and oxidant, the trifluoromethyloximation of alkenes proceeds smoothly in a free‐radical process. The developed difunctionalization reaction enables practical and efficient synthesis of a wide range of α‐CF 3 ketoximes in moderate yields with excellent regioselectivity. This method features the use of readily available and stable alkenes as substrates and inexpensive CF 3 SO 2 Na as a CF 3 reagent, no involvement of transition metals or external oxidant, and room‐temperature conditions. Moreover, a scale‐up of the reaction, further transformation of the products into various valuable CF 3 ‐containing compounds, and removal of the trifluoromethyl group are readily achieved.