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Catalytic Rearrangement of Aldoximes to Primary Amides in Environmentally Friendly Media under Thermal and Microwave Heating: Another Application of the Bis(allyl)-Ruthenium(IV) Dimer [{RuCl(μ-Cl)(η33-C10H16)}2]
Author(s) -
Pedro J. GonzálezListe,
Victorio Cadierno,
Sergio E. Garcı́a-Garrido
Publication year - 2015
Publication title -
acs sustainable chemistry and engineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.878
H-Index - 109
ISSN - 2168-0485
DOI - 10.1021/acssuschemeng.5b01107
Subject(s) - ruthenium , catalysis , chemistry , dimer , environmentally friendly , propynyl , organic chemistry , medicinal chemistry , primary (astronomy) , ecology , physics , astronomy , biology
The rearrangement of aldoximes to primary amides has been studied using the commercially available bis(allyl)-ruthenium(IV) complex [{RuCl(μ-Cl)(η3:η3-C10H16)}2] (1; C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) as a catalyst under thermal and microwave heating. The reactions proceeded cleanly in a mixture of water/glycerol (1:1) at 120–150 °C, without the assistance of any cocatalyst, affording the desired amides in moderate to high yields and short times. The process was operative with aromatic, heteroaromatic, aliphatic, and α,β-unsaturated aldoximes and tolerated the presence of several functional groups in the substrates. In addition, the recyclability of catalyst 1 (up to six consecutive runs) could be demonstrated.

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