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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Hauptverfasser: Zheng, Huiyuan (VerfasserIn) , Hao, Yue (VerfasserIn) , Wang, Yongqiang (VerfasserIn) , Zhao, Xue (VerfasserIn) , Zhao, Ximei (VerfasserIn) , Xu, Liang (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn) , Wang, Guanghui (VerfasserIn)
Dokumenttyp: Article (Journal) Editorial
Sprache:Englisch
Veröffentlicht: 29 August 2025
In: Organic letters
Year: 2025, Jahrgang: 27, Heft: 34, Pages: 9405-9411
ISSN:1523-7052
DOI:10.1021/acs.orglett.5c02683
Online-Zugang:Verlag, kostenfrei, Volltext: https://doi.org/10.1021/acs.orglett.5c02683
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Verfasserangaben:Huiyuan Zheng, Yue Hao, Yongqiang Wang, Xue Zhao, Ximei Zhao, Liang Xu, A. Stephen K. Hashmi, and Guanghui Wang

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520 |a 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. 
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