Sc(OTf)3-Catalyzed C2-Selective Cyanation/Defluorination Cascade of Perfluoroalkylated 3-Indolylmethanols and Application to the Synthesis of 3-Fluoro(perfluoroalkyl)-β-carbolines

被引：11
作者：
Sang, Jingjing [1 ]
Feng, Li [1 ]
Hu, Rui [1 ]
Chen, Jichao [1 ]
Shang, Dandan [1 ]
Bao, Qing [1 ]
Rao, Weidong [1 ]
机构：
[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 19期
基金：
中国国家自然科学基金;
关键词：
DIFLUOROMETHYL 2-PYRIDYL SULFONE; GEM-DIFLUOROOLEFINATION; C-F; DIAZO-COMPOUNDS; DIRECT CYANATION; DIFLUOROCARBENE; DIFLUOROALKENES; ALKYLATION; FUNCTIONALIZATION; ACTIVATION;
D O I：
10.1021/acs.orglett.1c02932
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unprecedented Sc(OTf)(3)-catalyzed C2-selective cyanation/defluorination cascade of perfluoroalkylated 3-indolylmethanols with TMSCN is described, which provides a novel and practical strategy for the synthesis of structurally diverse 3-(2-cyano)-indolyl substituted gem-difluoroalkenes and beta-fluoro-beta-perfluoroalkylalkenes. The reaction features excellent regio- and stereoselectivity and broad substrate scope. Notably, the obtained gem-difluoroalkenes and beta-fluoro-beta-perfluoroalkylalkenes could be easily transformed into 3-fluoro(perfluoroalkyl)-beta-carbolines with excellent efficiency simply by treating them with Grignard reagents or DIBAL-H under mild reaction conditions.
引用
收藏
页码：7666 / 7671
页数：6
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