C(sp<sup>2</sup>)–C(sp<sup>3</sup>) Suzuki–Miyaura Cross-Coupling Using <i>gem</i>-Bis(boronates)
A strategy utilizing <i>gem</i>-bis(boronates) as a stable and easily accessible surrogate for the analogous monoboronate and their efficient use in Suzuki-Miyaura cross-couplings to access the highly interesting 1,2-diaryl ethane motif is described. The general reactivity of <i>gem</i>-bis(boronates) and its advantages over monoboronate are demonstrated by a broad substrate scope and minimal β-hydride elimination side product formation. Cusparine, an antituberculosis natural product, was synthesized via this method with a shortened route, demonstrating its brevity, effectiveness, and scalability.
Authors
- Mengran Zhao
- Jason K. Dutra (ORCID: https://orcid.org/0000-0002-4563-5267)
- Ormacinda R. White (ORCID: https://orcid.org/0009-0008-7099-465X)
- John M. Curto (ORCID: https://orcid.org/0000-0001-9033-5952)
- Qingjian Zhang (ORCID: https://orcid.org/0009-0004-8248-3612)
- Kenneth J. DiRico
- Mingjun Jia (ORCID: https://orcid.org/0000-0002-5826-8662)
- Jun Xiao (ORCID: https://orcid.org/0009-0007-8649-8805)
- Duo Zhou
- Mengqing Wang (ORCID: https://orcid.org/0009-0003-1575-9052)
- Wen Xiu (ORCID: https://orcid.org/0000-0003-1040-4386)
Institutions
- Pfizer (United States) (US)
- Purdue University West Lafayette (US)
- WuXi AppTec (China) (CN)
- Université Bourgogne Franche-Comté (FR)
- Project Oceanology (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-09-30
- DOI
- https://doi.org/10.1021/acs.joc.5c01605
- Citations
- 1
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94