Sc(OTf)3-Catalyzed C–C Bond Cleavage of Unactivated Acylazaarenes with 1,2-Diamines to Afford Azaarenes and Imidazoles

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-25 DOI:10.1021/acs.orglett.5c00026

Bo Pang, Hai-Long Xin, Jeesoo Choi, Hiroyuki Morimoto, Takashi Ohshima

引用次数: 0

Abstract

We report a method for cleaving the C(O)–sp²C bonds of unactivated acylazaarenes via benzimidazoline intermediates using a mild redox neutral catalytic system involving scandium triflate. This method avoids the need for preactivation or transition metal catalysts, enabling efficient C–C bond cleavage in a broad range of substrates, including 2-acylimidazoles, 2-acylpyridines, 2-acylpyrole, and even nonchelating 3-acylindole, in which direct C–C bond cleavage has not been previously achieved.

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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.