Radical Functionalization of 1,6-Diene via Transannular Cyano Migration: Synthesis of Polysubstituted Cyclopentanes†

被引：0
|
作者：
Wang, Ziqiang [1 ,2 ,3 ]
Chen, Yasu [1 ,2 ]
Zhu, Chen [1 ,2 ,3 ]
机构：
[1] Shanghai Jiao Tong Univ, Zhangjiang Inst Adv Study, Frontiers Sci Ctr Transformat Mol, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[2] Shanghai Jiao Tong Univ, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[3] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2025年 / 43卷 / 04期
基金：
中国国家自然科学基金;
关键词：
Cyano migration; Cyclopentane; 1,6-Diene; Photoredox catalysis; Radical reactions; Radicals; Cyclization; Rearrangement; ENANTIOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITIONS; DIFUNCTIONALIZATION; ANNULATION; STRATEGY;
D O I：
10.1002/cjoc.202401072
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient transannular cyano migration is reported for gem-dicyano-1,6-diene, which is triggered by the addition of external arylsulfonyl radicals. The overall transformation proceeds through a sequence of intramolecular 5-exo-trig cyclization, suprafacial 1,4-cyano migration, and the capture by H or D atom, leading to the production of valuable polysubstituted cyclopentanes under mild photoredox catalytic conditions. The reaction is adapted to a wide range of sodium (hetero)arylsulfinates, demonstrating good functional group compatibility. This method provides a new protocol for radical-mediated functional group migration.
引用
收藏
页码：437 / 442
页数：6
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