Regioselective palladium-catalyzed synthesis of beta-arylated primary allylamine equivalents by an efficient Pd-N coordination.
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.
Olofsson
K
K
Department of Organic Pharmaceutical Chemistry, Uppsala University, BMC, Box 574, SE-75123 Uppsala, Sweden.
Sahlin
H
H
Larhed
M
M
Hallberg
A
A
D000499:Allylamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010165:Palladium; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D007202:Indicators and Reagents; D000499:Allylamine; D010165:Palladium