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J Org Chem. 2001 Jan 26;66(2):544-9.

Regioselective palladium-catalyzed synthesis of beta-arylated primary allylamine equivalents by an efficient Pd-N coordination.

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Department of Organic Pharmaceutical Chemistry, Uppsala University, BMC, Box 574, SE-75123 Uppsala, Sweden.


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.

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