Mechanistic details of the dehydrative carbon-heteroatom bond construction via the benzoisochalcogenazolone-catalyzed acylative oxidation-reduction-condensation strategy

被引：0

作者：

Lian, Deston R.

Liebeskind, Lanny S. ^{[1
]}

Musaev, Djamaladdin G. ^{[1
]}

机构：

[1] Emory Univ, Cherry L Emerson Ctr Sci Computat, 1521 Dickey Dr, Atlanta, GA 30322 USA

来源：

ARKIVOC | 2021年

关键词：

DFT Studies; oxidation-reduction-condensation; dehydrogenative regeneration; organochalcogens; dehydrative C-C coupling; CARBOXYLIC-ACIDS; PEROXYNITRITE ANION; EBSELEN; REACTIVITY; MITSUNOBU; DERIVATIVES; AMIDES;

D O I：

10.24820/ark.5550190.p011.406

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DFT has been used to study the mechanism, nature, and thermodynamics of each of the elementary steps of the redox dehydrative carbon-heteroatom bond formation via a benzoisochalcogenazolone-catalyzed oxidation-reduction-condensation strategy. It is shown that this reaction, in the absence of the carboxylic acid, proceeds via a deoxygenative dimerization pathway: the formation of new benzoisoselenazolone and benzoisotellurazolone deoxygenation dimers are predicted. In the presence of a carboxylic acid, this reaction leads to productive S-, Se-, and Te-ester formation. These calculations confirm regeneration of the oxidants to be an energy-demanding step of the overall reaction. [GRAPHICS]

引用

页码：44 / 52

页数：9