Remote desaturation of hexenenitriles by radical-mediated cyano migration

被引：17

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.

引用

页数：7

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