Enabling Bifunctionality and Hemilability of N-Heteroaryl NHC Complexes

Functionalized carbene ligands: Increasing the steric bulk of R1 on 1 from H to tBu results in lengthening of the MN bond (by up to 9 %), lowered activation energy for chelate opening (cf. 2) by 17 kcal mol−1, and improved binding of an amine and intramolecular hydrogen bonding (3). Iridium species...

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Published in:Chemistry : a European journal 2011-06, Vol.17 (24), p.6606-6609
Main Authors: Specht, Zephen G., Cortes-Llamas, Sara A., Tran, Hai N., van Niekerk, Christoffel J., Rancudo, Khing T., Golen, James A., Moore, Curtis E., Rheingold, Arnold L., Dwyer, Tammy J., Grotjahn, Douglas B.
Format: Article
Language:English
Subjects:
Amines
Bonding
Carbenes
Catalysis
Chelating
Chemistry
cyclization
Hydrogen bonding
Iridium
Ligands
N-heterocyclic carbenes
NMR spectroscopy
pendant base
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Summary:Functionalized carbene ligands: Increasing the steric bulk of R1 on 1 from H to tBu results in lengthening of the MN bond (by up to 9 %), lowered activation energy for chelate opening (cf. 2) by 17 kcal mol−1, and improved binding of an amine and intramolecular hydrogen bonding (3). Iridium species with R1=tBu are effective catalysts of base‐free intramolecular hydroamination, unlike less‐hindered analogues.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201100521