Please use this identifier to cite or link to this item: https://doi.org/10.1021/om9010966
Title: Syntheses, structures, and catalytic activities of hemilabile thioether-functionalized NHC complexes
Authors: Huynh, H.V. 
Yeo, C.H.
Chew, Y.X.
Issue Date: 22-Mar-2010
Citation: Huynh, H.V., Yeo, C.H., Chew, Y.X. (2010-03-22). Syntheses, structures, and catalytic activities of hemilabile thioether-functionalized NHC complexes. Organometallics 29 (6) : 1479-1486. ScholarBank@NUS Repository. https://doi.org/10.1021/om9010966
Abstract: Four imidazolium (5a/b) and benzimidazolium (6a/b) salts with hemilabile alkyl-aryl thioether functions have been prepared via a straightforward and modular pathway in order to compare their reactivities toward palladation. Reaction of 5a/b with Pd(OAc)2 gave complex product mixtures, whereas 6a/b afforded the desired bis(benzimidazolin-2-ylidene) complexes 8a/b in good yields. The difference in reactivities of benzimidazole versus imidazole derivatives was attributed to the presence of additional acidic protons at C4/5 positions of the imidazolium ring, leading to competing and unselective deprotonation reactions. The milder Ag-NHC transfer reaction, on the other hand, provided either mono- or bis(imidazolin-2-ylidene) complexes (9 or 7a/b) in good yields depending on the ligand:metal ratio. The interesting hemilability in monocarbene complex 9 was investigated by spectroscopy and thioether displacement reaction with PPh3, yielding the mixed. NHC-PPh 3 complex 1.0 in high yields. An initial, comparative catalytic study also reveals that the mixed-donor complex 1.0 exhibits the highest activity among the complexes tested. © 2010 American Chemical Society.
Source Title: Organometallics
URI: http://scholarbank.nus.edu.sg/handle/10635/95019
ISSN: 02767333
DOI: 10.1021/om9010966
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.

SCOPUSTM   
Citations

74
checked on Jul 9, 2018

WEB OF SCIENCETM
Citations

72
checked on Jul 9, 2018

Page view(s)

36
checked on Jun 29, 2018

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.