Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis

Organic Letters
Gianpiero CeraGiovanni Maestri

Abstract

The combination of a Pd(0) complex with benzoic acid converts propargylic tryptamines to the corresponding tetrahydro-β-carbolines. The method uses unprotected indoles and affords the desired products with ample functional group tolerance. Detailed modeling studies reveal a close synergy between the organic and metal catalysts, which enables sequential alkyne isomerization, indole C-H activation, and eventual C-C reductive elimination to afford the target heterocycles.

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Citations

Oct 13, 2018·Organic & Biomolecular Chemistry·Thaís ProchnowGilson Zeni
Jun 27, 2020·Chemical Communications : Chem Comm·Ding-Wei JiQing-An Chen

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