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Cross‐Dehydrogenative Coupling of Tetrahydroisoquinolines and 2‐Fluoro‐1,3‐benzodithiole‐1,1,3,3‐tetraoxide: A New Synthetic Approach to α‐Monofluoromethyl Tertiary Amines
Author(s) -
Huang Baoqin,
Chen Yuan,
Zhang Xuejing,
Yan Ming
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100537
Subject(s) - chemistry , tetrahydroisoquinoline , coupling reaction , reaction conditions , combinatorial chemistry , catalysis , organic chemistry
A cross dehydrogenative coupling reaction of tetrahydroisoquinolines with 2‐fluoro‐1,3‐benzodithiole‐1,1,3,3‐tetraoxide had been developed. CuBr/TBHP was identified as the best catalyst and oxidant. A variety of coupling products were obtained with good to excellent yields under mild reaction conditions. 1‐Monofluoromethyl tetrahydroisoquinoline derivatives were prepared via a subsequent desulfonylation with sodium amalgam. This method provides a new synthetic approach to α‐monofluoromethyl tertiary amines.