A Mechanistic Perspective on Photocatalytic EnT-Enabled C3-N-Heteroarylation of Aryl Quinoxaline via C(sp2)–C(sp2) Coupling

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-11 DOI:10.1021/acs.orglett.5c00933

Raju Mandal, Subhendu Ghosh, Swastik Laha, Pritishree Panigrahi, Kalishankar Bhattacharyya, Bhisma K. Patel

引用次数: 0

Abstract

An EnT-mediated C3-N-heteroarylation of 2-aryl quinoxalines via decarboxylative radical–radical cross-coupling (C(sp²)–C(sp²)) with oxime esters is presented. Upon photoactivation, the triplet energy of the photocatalyst is transferred to both reacting partners (oxime ester and 2-phenylquinoxaline). The excited oxime ester undergoes decarboxylative fragmentation to a C-centered N-heteroaryl radical and an N-centered imine radical. The former attacks the C3 site of the quinoxaline diradical, while the latter acts as a hydrogen atom abstractor (HAA). Computational studies revealed that C–C bond formation with the heteroaryl radical is energetically more favorable than C–N bond formation.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.