Regioselective Palladium-Catalyzed Synthesis of β-Arylated Primary Allylamine Equivalents by an Efficient Pd-N Coordination

K Olofsson, H Sahlin, M Larhed…

Index: Olofsson; Sahlin; Larhed; Hallberg Journal of Organic Chemistry, 2001 , vol. 66, # 2 p. 544 - 549

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Citation Number: 60

Abstract

A highly regioselective Heck arylation, utilizing aryl triflates and a palladium/dppf catalytic system, can be performed at the internal, β-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 ...