Magic Blue-Initiated SN2-Type Ring Opening of Activated Aziridines: Friedel-Crafts-Type Alkylation of Electron-Rich Arenes/Heteroarenes

被引：3
|
作者：
Kashyap, Suraj [1 ]
Singh, Bharat [1 ]
Ghorai, Manas K. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 16期
关键词：
EFFICIENT CATALYST; N-TOSYLAZIRIDINES; C-ARYLATION; HEXACHLOROANTIMONATE; INDOLES; 2-ARYLAZIRIDINES; CYCLOADDITION; REARRANGEMENT; ARENES; SALTS;
D O I：
10.1021/acs.joc.4c01101
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A transition metal-free, atom-economical, and highly stereospecific synthetic approach to Friedel-Crafts-type alkylation of arenes/heteroarenes has been developed. The protocol involves the catalytic aminium radical-cation salt (Magic Blue)-initiated S(N)2-type nucleophilic ring opening of activated aziridines with arenes/heteroarenes to give the corresponding 2,2-diarylethylamines up to 99% yield and 85% ee (for nonracemic aziridines) in a very short reaction time. Moreover, on reaction with 1,3-dimethylindole and benzofuran, aziridines undergo domino-ring-opening cyclization (DROC) to give the various biologically significant heterocyclic scaffolds in moderate to good yields.
引用
收藏
页码：11429 / 11445
页数：17
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