Markovnikov Protoborylation of Unactivated Terminal Alkenes via Copper-Guanidine Catalysis
Herein copper-catalyzed Markovnikov protoborylation of unactivated terminal alkenes was achieved through the employment of a bulky σ-donating guanidine ligand. The reaction demonstrated good tolerance to diverse functional groups and remarkable selectivity for branched borylation products (86:14-97:3) under ambient conditions, which enabled the synthesis of secondary alkyl boronates in grams with further valuable derivatizations. Mechanistic studies suggested the boryl insertion to C═C bonds via Cu-guanidine complex and ruled out the possibility of a diboration-protodeboronation process.
Authors
- Jinghua Tang (ORCID: https://orcid.org/0000-0003-3359-5891)
- Jin‐Yu Liu (ORCID: https://orcid.org/0000-0003-1075-1687)
- Jin Tao (ORCID: https://orcid.org/0000-0002-8481-3732)
- Yicen Ge (ORCID: https://orcid.org/0000-0003-0653-8701)
- Ai Zhang (ORCID: https://orcid.org/0000-0002-8308-9973)
- Jianmin Chen (ORCID: https://orcid.org/0000-0001-5859-3070)
- Xiaoyan Ma (ORCID: https://orcid.org/0000-0002-4352-5427)
- Ge Lin (ORCID: https://orcid.org/0000-0003-2443-528X)
- Siyu Jiang
- Huangfeng Zhang
Institutions
- Chengdu University of Technology (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-23
- DOI
- https://doi.org/10.1021/acs.joc.5c00691
- Citations
- 3
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.81