Gold-Catalyzed Highly Regioselective Cage B(9)-H Alkylation of <i>o</i>-Carboranes with 1,6-Enynes
Described herein is a gold-catalyzed regioselective B(9)-H alkylation of <i>o</i>-carboranes via regioselective insertion of <i>exo</i>-cyclopropyl gold carbenes, generated in situ by gold-catalyzed <i>5-exo-dig</i> cyclization of 1,6-enynes, into the cage B(9)-H bond of <i>o</i>-carboranes. This new protocol furnishes a broad range of B(9)-bicyclo[3.1.0]hexylmethyl-<i>o</i>-carboranes in moderate to good yields (up to 83%) with good to excellent regioselectivities (B(9)/B(8) up to 100:0). Besides, a gold-catalyzed regioselective cage B(9)-H alkylation of <i>m</i>-carboranes with 1,6-enynes is realized for the first time.
Authors
- Liang Xu (ORCID: https://orcid.org/0000-0002-7939-8108)
- Yue Hao (ORCID: https://orcid.org/0000-0002-5065-8906)
- Xue Zhao (ORCID: https://orcid.org/0000-0001-9281-7680)
- Ximei Zhao (ORCID: https://orcid.org/0000-0003-1792-8297)
- A. Stephen K. Hashmi (ORCID: https://orcid.org/0000-0002-6720-8602)
- Yong‐Qiang Wang
- Guanghui Wang (ORCID: https://orcid.org/0000-0001-5372-0165)
- Huiyuan Zheng
Institutions
- Shihezi University (CN)
- Ludong University (CN)
- Heidelberg University (DE)
- Xinjiang Production and Construction Corps (CN)
- Analytisches Laboratorium (DE)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-15
- DOI
- https://doi.org/10.1021/acs.orglett.5c02683
- Citations
- 2
- Primary Topic
- Boron Compounds in Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.72