Gold-Catalyzed Highly Regioselective Cage B(9)-H Alkylation of <i>o</i>-Carboranes with 1,6-Enynes
Huiyuan Zheng, Yue Hao, Yong‐Qiang Wang, Xue Zhao, Xue Zhao, Ximei Zhao, Ximei Zhao, Liang Xu, A. Stephen K. Hashmi, Guanghui Wang
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.
Topics & Concepts
ChemistryRegioselectivityAlkylationCageCatalysisMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryCombinatoricsMathematicsBoron Compounds in ChemistryOrganoboron and organosilicon chemistryPharmacological Effects and Toxicity Studies