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Gold-Catalyzed Highly Regioselective Cage B(9)-H Alkylation of o-Carboranes with 1,6-Enynes
Huiyuan Zheng1, Yue Hao1, Yongqiang Wang1
1School of Chemistry and Chemical Engineering, Ludong University, Yantai 264025, China.
Abstract:
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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