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.
Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis / Cera, Gianpiero; Lanzi, Matteo; Balestri, Davide; Della Ca, Nicola; Maggi, Raimondo; Bigi, Franca; Malacria, Max; Maestri, Giovanni. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 20:11(2018), pp. 3220-3224. [10.1021/acs.orglett.8b01072]
Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis
CERA, GIANPIERO;Lanzi, Matteo;Balestri, Davide;Della Ca, Nicola;Maggi, Raimondo;Bigi, Franca;Maestri, Giovanni
2018-01-01
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.| File | Dimensione | Formato | |
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