Remote desaturation of hexenenitriles by radical-mediated cyano migration

被引：10
|
作者：
Wang, Ziqiang [1 ]
Chang, Chenyang [1 ]
Chen, Yasu [2 ]
Wu, Xinxin [1 ]
Li, Jie [1 ]
Zhu, Chen [1 ,2 ]
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China
[2] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
来源：
TETRAHEDRON | 2023年 / 131卷
关键词：
Alkene difunctionalization; Cyano migration; Photochemistry; Radical reactions; Desaturation; UNACTIVATED ALKENES; 1,2-ARYL MIGRATION; DIFUNCTIONALIZATION; ALKYNYLATION; POTENTIALS; HETEROARYL; STRATEGY;
D O I：
10.1016/j.tet.2022.133228
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a new reaction mode involving functional group migration, which is applied to the radical -mediated remote desaturation of hexenenitriles. The reaction proceeds through consecutive alkene sulfonylation, intramolecular cyano migration, and single-electron oxidation of benzyl radical to cation followed by deprotonation, leading to a variety of densely functionalized alkenes. The protocol features mild photocatalytic conditions, broad functional group tolerance, and high product diversity.(c) 2022 Elsevier Ltd. All rights reserved.
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页数：7
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