Indol-2-Ylidene (IdY): A New Ambiphilic N-Heterocyclic Carbene Derived from Indole

15 October 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The ambiphilic 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.


N-heterocyclic carbene
ambiphilic carbene
copper catalysis

Supplementary materials



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