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Indol‐2‐ylidene (IdY): Ambiphilic N‐Heterocyclic Carbene Derived from Indole **
Author(s) -
Kim Hyunho,
Kim Minseop,
Song Hayoung,
Lee Eunsung
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004879
Subject(s) - carbene , regioselectivity , aryl , chemistry , alkyl , indole test , adduct , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The synthesis of ambiphilic N‐heterocyclic carbene ligand, indol‐2‐ylidene (IdY, A ), is described. A series of indolenium precursors ( 2 a – f ) were prepared on a gram scale in good yields. Trapping experiments with elemental selenium, [RhCl(cod)] 2 and CuCl provided the expected carbene adducts. Further computational and spectroscopic studies supported the ambiphilicity of IdY, which lies between cyclic (alkyl)(amino)carbenes (CAAC‐5) and cyclic (amino)(aryl)carbene (CAArC). The copper complexes ( 6 ) show high percent buried volume (% V bur = 58.1) and allow for carboboration of terminal alkynes within 30 minutes in a demonstration of synthetic utility with good yields and high regioselectivity.