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Published on: November 30, 2022
A General Sonogashira-Type Strategy for Exopolyhedral B-C(sp) Bond Formation on o- and m-Carboranes
Charis A Hinkle1, Aidan T Tiffany1, Alexander P Luancing1
1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
None:
We report our discovery that tricyclohexyl phosphine is a privileged ligand that enables highly efficient Pd-catalyzed B-C(sp) bond formation on iodinated carborane precursors. We display the generality and utility of our reaction framework in the alkynylation of 9-I-m-carborane and demonstrate the first examples of monoalkynylation and symmetric dialkynylation on 9-I-o-carborane and 9,10-I2-m-carborane, respectively, under Sonogashira-type cross-coupling conditions across a broad range of diverse and complex alkyne-terminated coupling partners.
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