Synthesis of N-H-Free 1,4-Dihydroisoquinoline-3(2H)-ones via Pd-Catalyzed C-H Olefination Using Polyfluorosulfinyl as the Auxiliary Group

被引：7
作者：
Chen, Yu-Hao [1 ]
Shao, Nan-Qi [2 ]
Li, Chen [1 ]
Wang, Dong-Hui [2 ]
机构：
[1] Wuyi Univ, Sch Biotech & Hlth Sci, Jiangmen 529020, Guangdong, Peoples R China
[2] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem,Ctr Excellence Mol Synth, CAS Key Lab Synthet & Selfassembly Chem Organ Fun, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 15期
基金：
国家重点研发计划;
关键词：
ACTIVATION; AMINES; BONDS;
D O I：
10.1021/acs.orglett.0c01979
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Pd(II)-catalyzed olefination of aryl C-H bonds with a self-cleaving 2-chlorotretafluoroethylsulfinyl (-SOCF2CF2Cl) auxiliary was developed. In the reaction mixture, the olefination products underwent in situ Michael addition and the subsequent expulsion of the auxiliary to provide the N-H-free 1,4-dihydroisoquinoline-3(2H)-one products. Mechanistic studies reveal that the auxiliary group is crucial for C-H activation, and Na2CO3 and an alcoholic solvent play key roles in facilitating the cleavage of the polyfluoroalkylsulfinyl auxiliary.
引用
收藏
页码：5880 / 5884
页数：5
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