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- Title
Indol‐2‐ylidene (IdY): Ambiphilic N‐Heterocyclic Carbene Derived from Indole**.
- Authors
Kim, Hyunho; Kim, Minseop; Song, Hayoung; Lee, Eunsung
- Abstract
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 (% Vbur = 58.1) and allow for carboboration of terminal alkynes within 30 minutes in a demonstration of synthetic utility with good yields and high regioselectivity.
- Subjects
COPPER compounds; CARBENES; SELENIUM; ALKYNES; CARBENE synthesis
- Publication
Chemistry - A European Journal, 2021, Vol 27, Issue 11, p3849
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202004879