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

15 October 2020, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

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.

Keywords

N-heterocyclic carbene
ambiphilic carbene
copper catalysis

Supplementary materials

Title
Description
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Title
SI-Indol-2-ylidene
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Now Published

Indol‐2‐ylidene (IdY): Ambiphilic N‐Heterocyclic Carbene Derived from Indole** [opens in a new tab]
Hyunho Kim, Minseop Kim, Hayoung Song, Eunsung Lee journal article
Chemistry – A European Journal , Volume 27, Issue 11
Online publication date: Jan 15, 2021

Version History

Oct 15, 2020 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.13093529.v1
D O I: 10.26434/chemrxiv.13093529.v1 [opens in a new tab]

Author’s competing interest statement

The authors declare no conflict of interest.

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