Cobalt-catalyzed direct transformation of aldehydes to esters: the crucial role of an enone as a mediator

被引：8
作者：
Jiang, Biao-Lin [1 ,2 ]
Lin, Yang [2 ,3 ]
Wang, Meng-Liang [1 ]
Liu, Dian-Sheng [1 ]
Xu, Bao-Hua [2 ]
Zhang, Suo-Jiang [2 ]
机构：
[1] Shanxi Univ, Sch Chem & Chem Engn, Taiyuan 030006, Shanxi, Peoples R China
[2] Chinese Acad Sci, Inst Proc Engn, State Key Lab Multiphase Complex Syst, Beijing Key Lab Ion Liquids Clean Proc,Key Lab Gr, Beijing 100190, Peoples R China
[3] East China Univ Sci & Technol, State Key Lab Chem Engn, Shanghai 200237, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 06期
基金：
中国国家自然科学基金;
关键词：
CHEMOSELECTIVE TRANSFER HYDROGENATION; C-H FUNCTIONALIZATION; OXIDATIVE ESTERIFICATION; TISHCHENKO REACTIONS; PRIMARY ALCOHOLS; INTERMOLECULAR HYDROACYLATION; INTRAMOLECULAR HYDROACYLATION; ALDOL CONDENSATIONS; BENZYLIC ALCOHOLS; COMPLEXES;
D O I：
10.1039/c8qo01298a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An oxidative esterification of aldehydes with alkanols catalyzed by an in situ generated low-valent cobalt system has been developed using an enone as a mild oxidant. Mechanistic studies revealed that it proceeds through a Co(i)-catalyzed hydrogen-transfer route, wherein the -vinyl moiety in the bidentate enone functions as a hydride acceptor. Meanwhile, Co(i)-catalyzed formyl C-H activation occurred as a competing reaction leading to aldehyde dimerization. The occurrence of the usually kinetically disfavored hydride transfer step therein was significantly increased in the presence of an enone reacting as a hydride transfer initiator.
引用
收藏
页码：801 / 807
页数：7
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