Tryptamine synthesis by iron‐porphyrin catalyzed C—H functionalization of indole with diazoacetonitrile

The functionalization of C—H bonds with non‐precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron‐porphyrin catalyzed reactions of diazoacetonitrile with N‐heterocycles yielding important precursors of tryptamines including experimental mechanistic studies and proof‐of‐concept studies of an enzymatic protocol with YfeX enzyme. Using readily available FeTPPCl we achieved a highly efficient C—H functionalization of indole and indazole heterocycles. This transformation features mild reaction conditions, excellent yields with broad functional group tolerance, including gram‐scale applications giving a unique streamlined access to tryptamines.

from A via a.sfakia on Inoreader http://bit.ly/2SfEoQ0