Tandem Azolation/Aromatization of Tetrahydronaphthalenes with Hydrogen Evolution via Organophotoredox/Cobalt Dual Catalysis

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-27 DOI:10.1021/acs.orglett.5c00640

Cheng Huang, Sheng Tang, Chen-Lu Wang, Chen Kang, Ying Wang, Yaru Jing, Zhong-Ming Ye, Zhenhong Wei, Hu Cai

引用次数: 0

Abstract

Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of N-(β-naphthyl)azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, step- and atom-economy, and site-selectivity. A preliminary mechanistic study has uncovered that the transformation undergoes a N-centered radical mediated C–H/N–H cross-coupling followed by dehydrogenative aromatization of saturated naphthyl surrogates under visible light irradiation, and DFT calculations elucidate the site-selectivity.

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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.