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 | Zendy

Huang Baoqin | Zendy; Chen Yuan | Zendy; Zhang Xuejing | Zendy; Yan Ming | Zendy

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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.

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