Dual Photoexcited Palladium and Photoredox-Catalyzed Remote C(sp3)–H Acylation of Hydroxyamides

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-20 DOI:10.1021/acs.orglett.5c00881

Daling Li, Jun Wei, Lixu Ren, Lingmin Zhou, Liya Huang, Ying Yu, Siping Wei, Na Hao, Jun Wang, Lin Yang, Xianchao Pan, Qiang Fu, Ji Lu

引用次数: 0

Abstract

Herein, we report an unprecedented dual photoexcited palladium and photoredox-catalyzed remote C(sp³)–H acylation of amides free of external acylating reagents through sequential N–O/C–H/C–O bond cleavage and chemoselective C–C bond formation. This dual catalytic system shows high efficiency, good atom economy by deletion of oxygen, and diverse functional group tolerance. Experimental investigation of the reaction mechanism revealed that O-acyl hydroxamides enabled by photoexcited palladium generated the alkyl radicals via a 1,5-HAT process mediated by amidyl radicals and a palladium carboxylate complex, which, undergoing photoredox-catalyzed phosphoranyl radical-mediated C–O bond cleavage, leads to coupling with alkyl radicals to deliver the final products.

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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.