Tryptamine Synthesis by Iron Porphyrin Catalyzed C−H Functionalization of Indoles with Diazoacetonitrile

Title data

Hock, Katharina J. ; Knorrscheidt, Anja ; Hommelsheim, Renè ; Ho, Junming ; Weissenborn, Martin J. ; Koenigs, Rene M.:
Tryptamine Synthesis by Iron Porphyrin Catalyzed C−H Functionalization of Indoles with Diazoacetonitrile.
In: Angewandte Chemie International Edition. Vol. 58 (2019) . - pp. 3630-3634.
ISSN 1521-3773
DOI: https://doi.org/10.1002/anie.201813631

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Abstract in another language

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, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C−H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.