Efficient ruthenium-catalyzed aerobic oxidation of amines by using a biomimetic coupled catalytic system.
2005 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 11, no 8, 2327-2334 p.Article in journal (Refereed) Published
Efficient aerobic oxidn. of amines was developed using a biomimetic coupled catalytic system involving a Ru-induced dehydrogenation. The principle for this aerobic oxidn. is that the electron transfer from the amine to O2 occurs stepwise via coupled redox systems and this leads to a low-energy electron transfer. A substrate-selective Ru catalyst dehydrogenates the amine and the H atoms abstracted are transported to an electron-rich quinone (2a; 2,6-dimethoxy-p-benzoquinone). The hydroquinone thus formed is subsequently reoxidized by air with the aid of an oxygen-activating [Co(salen)]-type complex (27; [Co(MeN(CH2CH2CH2N:CHC6H4O-2)2)]). The reaction can be used for the prepn. of ketimines and aldimines in good to high yields from the appropriate corresponding amines. The reaction proceeds with high selectivity, and the catalytic system tolerates air without being deactivated. The rate of the dehydrogenation was studied by using quinone 2a as the terminal oxidant. A catalytic cycle in which the amine promotes the dissocn. of the dimeric catalyst (OC)2(Î·5-Ph4C5OH)Ru(ÎŒ-H)Ru(Î·5-OC5Ph4)(CO)2 is presented. [on SciFinder(R)]
Place, publisher, year, edition, pages
2005. Vol. 11, no 8, 2327-2334 p.
amine aerobic oxidn ruthenium catalysis biomimetic coupled catalytic system, aldimine ketimine synthesis amine aerobic dehydrogenation biomimetic coupled catalysis, cobalt salen complex oxygen activating amine aerobic oxidn
IdentifiersURN: urn:nbn:se:uu:diva-174522DOI: 10.1002/chem.200401082OAI: oai:DiVA.org:uu-174522DiVA: diva2:527598
CAPLUS AN 2005:364389(Journal)2012-05-212012-05-212012-05-21