Fe/Mn-Synergistic Promoted C(sp<sup>3</sup>)–Bi Cross-Coupling of Alkyl Chlorides with Chlorobismuthanes to Access Air-Stable Alkylbismuthanes
Alkylating bismuthanes containing C(sp<sup>3</sup>)-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(sp<sup>3</sup>)-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(sp<sup>3</sup>)-C(sp<sup>2</sup>), C(sp<sup>3</sup>)-Se, C(sp<sup>3</sup>)-S, and C(sp<sup>3</sup>)-N bonds.
Authors
- Renhua Qiu (ORCID: https://orcid.org/0000-0002-8423-9988)
- Nobuaki Kambe (ORCID: https://orcid.org/0000-0002-2887-9489)
- Liyuan Le
- Youwen Chen (ORCID: https://orcid.org/0000-0003-4949-8471)
- Wei Deng (ORCID: https://orcid.org/0000-0002-5972-560X)
- Shuang‐Feng Yin (ORCID: https://orcid.org/0000-0001-9857-9804)
- Shuangshuang Li (ORCID: https://orcid.org/0000-0003-2702-1293)
Institutions
- Central South University of Forestry and Technology (CN)
- Hunan International Economics University (CN)
- Hunan University (CN)
- Chemo (France) (FR)
- State Key Laboratory of Chemobiosensing and Chemometrics (CN)
- Graduate School USA (US)
- The University of Osaka (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-28
- DOI
- https://doi.org/10.1021/acs.orglett.5c00623
- Citations
- 1
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China