通过亚胺的Minisci型反应将醛一锅法转化为酮

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

作者信息

Rubanov Zakhar M, Levin Vitalij V, Dilman Alexander D

机构信息

N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.

Mendeleev University of Chemical Technology, Miusskaya Sq., 9, Moscow 125047, Russian Federation.

出版信息

Org Lett. 2023 Dec 8;25(48):8751-8755. doi: 10.1021/acs.orglett.3c03764. Epub 2023 Nov 28.

DOI:10.1021/acs.orglett.3c03764

PMID:38016095

Abstract

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 -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.

摘要

描述了一种通过醛亚胺的初步形成将醛转化为酮的方法。亚胺参与了在光氧化还原条件下与由羟基邻苯二甲酰亚胺酯产生的烷基自由基进行的酸促进的Minisci型反应。在亚胺离子加成后形成的氨基自由基阳离子被认为是决定反应结果的关键中间体。