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J Am Chem Soc. 2006 Jun 21;128(24):7728-9.

Nickel-mediated regioselective [2 + 2 + 2] cycloaddition of carboryne with alkynes.

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  • 1Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territory, Hong Kong, China.


Transition metal-benzyne complexes have found many applications in organic synthesis, mechanistic studies, and the synthesis of functional materials. In sharp contrast, the chemistry of transition metal-carboryne complexes, especially late transition metal complexes, is virtually unknown. This communication reports a novel nickel-mediated regioselective [2 + 2 + 2] cycloaddition reaction of carboryne with alkynes via the Ni-carboryne intermediate (eta2-C2B10H10)Ni(PPh3)2. Because of the bulkiness of the carborane moiety, a high regioselectivity was achieved in the reactions involving unsymmetrical alkynes. This work furnishes a novel method for the preparation of highly substituted benzocarboranes which are difficult to obtain by other methods.

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