Superbase promoted direct N-Carbonylation of pyrrole with carbonic acid diesters

Carbonic acid diesters have been investigated as carbonylating agents in the direct reaction with pyrrole (HetNH). In the presence of superbases (DBU, P1-t-Bu, BTPP) as catalysts, the heteroaromatic substrate can be N-carbonylated by direct reaction with carbonic acid diesters under not-severe exper...

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Bibliographic Details
Published in:Tetrahedron Letters
Main Authors: CARAFA M, DISTASO M, MELE V, TRANI F, QUARANTA, Eugenio
Other Authors: Carafa, M, Distaso, M, Mele, V, Trani, F, Quaranta, Eugenio
Format: Article in Journal/Newspaper
Language:English
Published: 2008
Subjects:
organic carbonate
catalysi
pyrrole
carbonylation
phosgene substitution
Carbonic acid
Online Access:http://hdl.handle.net/11586/75287
https://doi.org/10.1016/j.tetlet.2008.03.129
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Summary:Carbonic acid diesters have been investigated as carbonylating agents in the direct reaction with pyrrole (HetNH). In the presence of superbases (DBU, P1-t-Bu, BTPP) as catalysts, the heteroaromatic substrate can be N-carbonylated by direct reaction with carbonic acid diesters under not-severe experimental conditions. The carbonylation reaction makes accessible pyrrole N-carbonyl derivatives (Het- NC(O)OR, (HetN)2CO) selectively through a simple straightforward way, which offers a safe eco-friendly alternative to the traditional synthetic methods based on hazardous phosgene or phosgene-derivatives.

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