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N-heterocyclic carbene ligand, indol-2-ylidene (IdY, A), is described. A series of indolenium precursors (2a-f)
were prepared on a gram scale in good yields. Trapping experiments with
elemental selenium, [RhCl(cod)]2 and CuCl lead to IdY-supported
materials, respectively. Computational and spectroscopic studies revealed the
ambiphilicity of IdY. The copper complexes (6) show high percent buried volume (%Vbur = 58.1) and
allow for carboboration of terminal alkynes within 30 minutes as synthetically
useful yields and high regioselectivity.