One-Pot Transformation of Aldehydes to Ketones via Minisci-Type Reaction of Imines

被引:8
|
作者
Rubanov, Zakhar M. [1 ]
Levin, Vitalij V. [1 ]
Dilman, Alexander D. [1 ]
机构
[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia
关键词
C(SP(2))-H FUNCTIONALIZATION; RADICAL-ADDITION; BOND;
D O I
10.1021/acs.orglett.3c03764
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the conversion of aldehydes to ketones via the preliminary formation of aldiminines is described. The imines are involved in acid promoted Minisci-type reaction with alkyl radicals generated from esters of N-hydroxylphthalimide under photoredox conditions. Aminyl radical cations formed after the addition of the iminium ions are believed to be key intermediates, which determine the reaction outcome.
引用
收藏
页码:8751 / 8755
页数:5
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