Open AccessBase-Promoted Radical Azofluoromethylation of Unactivated Alkenes
Author(s) -
Zhichao Lu,
Olivia Hennis,
Joseph Gentry,
Bo Xu,
Gerald B. Hammond
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c01395
Subject(s) - radical , chemistry , aryl , functional group , base (topology) , molecule , combinatorial chemistry , compatibility (geochemistry) , aryl radical , organic chemistry , photochemistry , chemical engineering , alkyl , mathematical analysis , mathematics , engineering , polymer
The base-induced reaction of aryl diazonium salts with commercially available CF 3 SO 2 Na/CF 2 HSO 2 Na allows for the generation of the corresponding diazene radicals along with fluoromethyl radicals. The addition of fluoromethyl radicals to alkenes with subsequent diazene trapping provides the azofluoromethylation products in good to excellent yields. This metal-free method under mild reaction conditions has broad functional group compatibility and is applicable in the late-stage modification of various natural products and bioactive molecules.