N-Heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement: synthesis of aryl salicylates from O-aryl salicylaldehydes

被引：61
作者：
Xia, Zi-Hao [1 ,2 ]
Dai, Lei [1 ,2 ]
Gao, Zhong-Hua [1 ,2 ]
Ye, Song [1 ,2 ]
机构：
[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, CAS Res Educ Ctr Excellence Mol Sci,Inst Chem, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 10期
基金：
中国国家自然科学基金;
关键词：
VISIBLE-LIGHT PHOTOREDOX; ALPHA; BETA-UNSATURATED ALDEHYDES; CATALYZED OXIDATIONS; NHC; EFFICIENT; ENALS; ALCOHOLS; ESTERS; ORGANOCATALYSIS; PHOTOCATALYSIS;
D O I：
10.1039/c9cc09272b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The N-heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement of O-aryl salicylaldehydes was developed. Both electron-deficient and electron-rich aryls worked well as migrating groups, giving the corresponding aryl salicylates in good yields. This reaction features formation of two new C-O bonds and one C-O bond cleavage via metal-free oxidation of the Breslow intermediate using oxygen as the terminal oxidant and following the Smiles rearrangement under photocatalysis.
引用
收藏
页码：1525 / 1528
页数：4
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