化学
酰胺
催化作用
基础(拓扑)
联轴节(管道)
药物化学
立体化学
高分子化学
有机化学
数学
机械工程
工程类
数学分析
作者
Masanori Shigeno,Kunihito Nakaji,Kanako Nozawa‐Kumada,Yoshinori Kondo
出处
期刊:Organic Letters
[American Chemical Society]
日期:2019-04-05
卷期号:21 (8): 2588-2592
被引量:26
标识
DOI:10.1021/acs.orglett.9b00550
摘要
This paper describes that an amide-base generated in situ from tetramethylammonium fluoride (TMAF) and N(TMS)3 catalyzes the deprotonative coupling of benzylic C(sp3)-H bonds with carbonyls to form stilbenes. A variety of methylheteroarenes (2-methylbenzothiophene, 2-methylbenzofuran, and 2-, 3-, or 4-methylpyridines) are used as nucleophiles. Application to enamine synthesis using DMF as an electrophile is also shown. The present system is effective for toluenes (4-phenyl-, 4-bromo-, 2-bromo-, and 4-chlorotoluenes) having low reactivity.
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