Regioselective palladium-catalyzed synthesis of beta-arylated primary allylamine equivalents by an efficient Pd-N coordination
2001 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 2, 544-549 p.Article in journal (Refereed) PublishedText
A highly regioselective Heck arylation, utilizing aryl triflates and a palladium/dppf catalytic system, can be performed at the internal, beta -carbon of Boc- and phthalimido-protected allylamines, yielding arylated primary allylamine equivalents. The very high regioselectivity obtained with secondary Boc-protected allylamides is suggested to be caused by an efficient coordination between an anionic nitrogen and palladium. Single-mode microwave irradiation has been utilized to shorten the reaction times and, in the case of Boc-protected allylamides, to improve the yields of two electron-poor aryl triflates.
Place, publisher, year, edition, pages
Uppsala Univ, BMC, Dept Organ Pharmaceut Chem, SE-75123 Uppsala, Sweden., 2001. Vol. 66, no 2, 544-549 p.
IdentifiersURN: urn:nbn:se:uu:diva-275425DOI: 10.1021/jo001416yISI: 000166560600027PubMedID: 11429827OAI: oai:DiVA.org:uu-275425DiVA: diva2:900260