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Gold-catalyzed highly regioselective cage B(9)-H alkylation of o-carboranes with 1,6-enynes

Described herein is a gold-catalyzed regioselective B(9)-H alkylation of o-carboranes via regioselective insertion of exo-cyclopropyl gold carbenes, generated in situ by gold-catalyzed 5-exo-dig cyclization of 1,6-enynes, into the cage B(9)-H bond of o-carboranes. This new protocol furnishes a broad...

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Main Authors: Zheng, Huiyuan (Author) , Hao, Yue (Author) , Wang, Yongqiang (Author) , Zhao, Xue (Author) , Zhao, Ximei (Author) , Xu, Liang (Author) , Hashmi, A. Stephen K. (Author) , Wang, Guanghui (Author)
Format: Article (Journal) Editorial
Language:English
Published: 29 August 2025
In: Organic letters
Year: 2025, Volume: 27, Issue: 34, Pages: 9405-9411
ISSN:1523-7052
DOI:10.1021/acs.orglett.5c02683
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1021/acs.orglett.5c02683
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Author Notes:Huiyuan Zheng, Yue Hao, Yongqiang Wang, Xue Zhao, Ximei Zhao, Liang Xu, A. Stephen K. Hashmi, and Guanghui Wang
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Summary:Described herein is a gold-catalyzed regioselective B(9)-H alkylation of o-carboranes via regioselective insertion of exo-cyclopropyl gold carbenes, generated in situ by gold-catalyzed 5-exo-dig cyclization of 1,6-enynes, into the cage B(9)-H bond of o-carboranes. This new protocol furnishes a broad range of B(9)-bicyclo[3.1.0]hexylmethyl-o-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 m-carboranes with 1,6-enynes is realized for the first time.
Item Description:Online veröffentlicht: 15. August 2025
Gesehen am 12.01.2026
Physical Description:Online Resource
ISSN:1523-7052
DOI:10.1021/acs.orglett.5c02683

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