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(η 6 ‐Arene)ruthenium(N‐heterocyclic carbene) Complexes for the Chelation‐Assisted Arylation and Deuteration of Arylpyridines: Catalytic Studies and Mechanistic Insights
Author(s) -
Prades Amparo,
Poyatos Macarena,
Peris Eduardo
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000049
Subject(s) - ruthenium , chemistry , carbene , regioselectivity , catalysis , combinatorial chemistry , kinetic isotope effect , limiting , deuterium , medicinal chemistry , stereochemistry , organic chemistry , mechanical engineering , physics , quantum mechanics , engineering
A series of (η 6 ‐arene)ruthenium complexes have been tested in the arylation of arylpyridines. One (η 6 ‐ 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.