(η6-Arene)ruthenium(N-heterocyclic carbene) Complexes for the Chelation-Assisted Arylation and Deuteration of Arylpyridines: Catalytic Studies and Mechanistic Insights
comunitat-uji-handle:10234/9
comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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http://dx.doi.org/10.1002/adsc.201000049 |
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Title
(η6-Arene)ruthenium(N-heterocyclic carbene) Complexes for the Chelation-Assisted Arylation and Deuteration of Arylpyridines: Catalytic Studies and Mechanistic InsightsDate
2010Publisher
Wiley-VCHISSN
1615-4150Bibliographic citation
Advanced Synthesis & Catalysis (2010), 352, 7, p. 1155-1162Type
info:eu-repo/semantics/articlePublisher version
http://onlinelibrary.wiley.com/doi/10.1002/adsc.201000049/abstractSubject
Abstract
A series of (η6-arene)ruthenium complexes have been tested in the arylation of arylpyridines. One (η6-p-cymene)ruthenium(N-heterocyclic carbene) complex (labelled as 1 in the text) was found to be the most effective, ... [+]
A series of (η6-arene)ruthenium complexes have been tested in the arylation of arylpyridines. One (η6-p-cymene)ruthenium(N-heterocyclic carbene) complex (labelled as 1 in the text) was found to be the most effective, being capable of arylating a wide set of substantially different arylpyridines. Complex 1 is also able to promote the regioselective deuteration of a series of arylated N-heterocycles, via a nitrogen-directed mechanism. Two of the deuterated amines were used to measure the kinetic isotope effect (KIE) in the arylation process. The detection of an inverse KIE, together with the observation that the CH activation process does not require the addition of a base, suggest that the rate-limiting step in the arylation process may be different to that of previously reported studies. [-]
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Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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