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

作　　者：Ziqiang Wang Yasu Chen Chen Zhu 

机构地区：[1]Frontiers Science Center for Transformative Molecules,Zhangjiang Institute for Advanced Study,and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs,Shanghai Jiao Tong University,800 Dongchuan Road,Shanghai 200240,China [2]Key Laboratory of Organic Synthesis of Jiangsu Province,College of Chemistry,Chemical Engineering and Materials Science,Soochow University,199 Ren-Ai Road,Suzhou,Jiangsu 215123,China

出　　处：《Chinese Journal of Chemistry》2025年第4期437-442,共6页中国化学(英文版)

基　　金：the National Natural Science Foundation of China(22171201 and 22371185);the Fundamental Research Funds for the Central Universities(23x010301599,24x010301678);the Program of Shanghai Academic/Technology Research Leader(23XD1421900).

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.

关 键 词：Cyano migration CYCLOPENTANE 1 6-Diene Photoredox catalysis Radical reactions Radicals CYCLIZATION Rearrangement 

分 类 号：O62[理学—有机化学]