Fe/Mn-Synergistic Promoted C(sp3)–Bi Cross-Coupling of Alkyl Chlorides with Chlorobismuthanes to Access Air-Stable Alkylbismuthanes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-28 DOI:10.1021/acs.orglett.5c00623

Youwen Chen, Shuangshuang Li, Liyuan Le, Shuang-Feng Yin, Wei Deng, Nobuaki Kambe, Renhua Qiu

引用次数: 0

Abstract

Alkylating bismuthanes containing C(sp³)–Bi bonds were first disclosed as early as 1850, but their development remains severely limited, especially the synthetic method. Herein, we developed the first Fe/Mn-synergistic promoted C(sp³)–Bi cross-coupling of alkyl halides with chlorobismuthanes, which can access alkylbismuthanes in satisfactory yields with various functional group compatibility (cyano, ester, aldehyde, and amide). Inactivated alkyl chlorides/bromides, as well as cyclic and acyclic alkyl electrophiles, smoothly yielded the corresponding products. Gram-scale synthesis and late-stage modification of drug molecules were also conducted. The synthesized alkylbismuthanes also could be alkylation reagents toward C(sp³)–C(sp²), C(sp³)–Se, C(sp³)–S, and C(sp³)–N bonds.

Abstract Image

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

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.