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

被引：7
作者：
Huang, Bao-qin [1 ]
Chen, Yuan [2 ,3 ]
Zhang, Xue-jing [1 ]
Yan, Ming [1 ]
机构：
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab Chiral Mol & Drug Discover, Guangzhou 510006, Peoples R China
[2] Nankai Univ, Coll Pharm, State Key Lab Med Chem Biol, Tianjin 300353, Peoples R China
[3] Nankai Univ, Tianjin Key Lab Mol Drug Res, Tianjin 300353, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 21期
基金：
中国国家自然科学基金;
关键词：
NUCLEOPHILIC MONOFLUOROMETHYLATION; FLUOROALKYLATION REACTIONS; FLUOROMETHYLATION; DESIGN;
D O I：
10.1002/ejoc.202100537
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 alpha-monofluoromethyl tertiary amines.
引用
收藏
页码：3015 / 3022
页数：8
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