Gold-catalyzed approach achieves regioselective alkylation of B(9)-H in carboranes, suggesting new synthetic routes.
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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Zheng et al. (2025) studied this question.
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