N-Alkylation of phenethylamine and tryptamine.
A clean and efficient method for the N-alkylation of tryptamine and phenethylamine, employing alcohols as the alkylating agents, has been developed. The reaction proceeds via catalytic electronic activation, involving an iridium catalyst which activates the alcohol by borrowing hydrogen from the substrate, returning it later in the catalytic cycle. Some examples of N-heterocyclisation have been performed employing a diol as the substrate.
Cami-Kobeci
Gerta
G
Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK.
Slatford
Paul A
PA
Whittlesey
Michael K
MK
Williams
Jonathan M J
JM
D000438:Alcohols / Q000737:chemistry; D000478:Alkylation; D003500:Cyclization; D010627:Phenethylamines / Q000138:chemical synthesis* / Q000737:chemistry; D014363:Tryptamines / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D010627:Phenethylamines; D014363:Tryptamines; C029261:phenethylamine; C030820:tryptamine