Radical heteroarylation of unactivated remote C(sp3)-H bonds via intramolecular heteroaryl migration

被引：11
|
作者：
Cao, Zhu [1 ]
Zhang, Huihui [1 ]
Wu, Xinxin [1 ]
Li, Yahong [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] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 22期
基金：
中国国家自然科学基金;
关键词：
C-H; HYDROGEN-ATOM; FUNCTIONALIZATION; ALKENES; DIFUNCTIONALIZATION; VINYLATION;
D O I：
10.1039/d1qo01209f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The radical-mediated heteroarylation of unactivated remote C(sp(3))-H bonds via intramolecular heteroaryl migration is achieved, leading to a variety of heteroaryl-substituted aliphatic ketones. A library of O-/S-/N-containing heteroaryls such as benzofuryl, benzothiazolyl, benzothienyl, benzoxazolyl, oxazolyl, and thiazolyl are amenable to the migration approach. The heteroaryl migration is triggered by an azido radical-mediated hydrogen atom abstraction from unactivated aliphatic C(sp(3))-H bonds. The transformation features mild C-C bond cleavage, good selectivity for tertiary C(sp(3))-H bonds, and broad functional group compatibility.
引用
收藏
页码：6395 / 6399
页数：5
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