Lewis acid catalyzed amino-Claisen rearrangement:A facile one pot synthesis of 2-allylarylamines from N-allylarylamines

摘要

Boron trifluoride-diethyl ether complex efficiently catalyzes a variety of amino-Claisen rearrangements of N-allylarylamines 1a-g to afford 2-allylarylamines 2a-g in moderate to good yields.A'-allylarylamines having electron deficient substituents undergo rearrangement at lower temperature than electron rich ones.2-AUylarylamines are useful synthons in palladium induced heteroannulation to give indoles'.In a quest to explore the feasibility of other amine substrates in this synthesis,a good method was required for the preparation of 2-allylarylamines.