Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-12835
Luan, X; Mariz, R; Gatti, M; Costabile, C; Poater, A; Cavallo, L; Linden, A; Dorta, R (2008). Identification and characterization of a new family of catalytically highly active imidazolin-2-ylidenes. Journal of the American Chemical Society, 130(21):6848-6858.
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A new class of easily accessible and stable imidazolin-2-ylidenes has been synthesized where the side chains are comprised of substituted naphthyl units. Introduction of the naphthyl groups generates C 2 -symmetric ( rac) and C s- symmetric ( meso) atropisomers, and interconversion between the isomers is studied in detail both experimentally and computationally. Complete characterization of the carbenes includes rare examples of crystallographically characterized saturated NHC structures. Steric properties of the ligands and an investigation of their stability are also presented. In catalysis, the new ligands show versatility comparable to the most widely used NHCs IMes/SIMes or IPr/SIPr. Excellent catalytic results are obtained when either the NHC salts (ring-opening alkylation of epoxides), NHC-modified palladium compounds (C-C and C-N cross-couplings), or NHC-ruthenium complexes (ring-closing metathesis, RCM) are employed. In several cases, this new ligand family provides catalytic systems of higher reactivity than that observed with previously reported NHC compounds.
|Item Type:||Journal Article, refereed, original work|
|Communities & Collections:||07 Faculty of Science > Institute of Organic Chemistry|
|Deposited On:||15 Feb 2009 11:47|
|Last Modified:||27 Nov 2013 20:06|
|Publisher:||American Chemical Society|
|Citations:||Web of Science®. Times Cited: 50|
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