Solventless selective phosgene-free N-carbonylation of N-heteroaromatics (pyrrole, indole, carbazole) under mild conditions

Literature Information

Publication Date 2012-10-15
DOI 10.1039/C2GC36103E
Impact Factor 10.182
Authors

Marianna Carafa, Francesco Iannone, Valentina Mele, Eugenio Quaranta


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Abstract

N-Heteroaromatics HetNH, such as pyrrole (1), indole (2) and carbazole (3), have been selectively N-carbonylated by a direct reaction with diphenyl carbonate (DPC), used as an environmental friendly carbonyl active species in place of toxic and hazardous phosgene. The carbonylation reaction can be effectively catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), which can act as a base catalyst by activating the HetNH substrate, and as a nucleophile catalyst by activating the organic carbonate. The influence of reaction parameters (temperature, reaction time, DBU load, DPC/HetNH molar ratio) on the productivity of the process has been also investigated. The synthetic methodology does not require severe temperature conditions, is solventless, simple (only one step), efficient and selective, and offers a new solution to the synthesis of synthetically versatile HetNCO2Ph derivatives through a route alternative to the current traditional phosgenation methods.

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