Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 14, Pages 1902-1910Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700165
Keywords
C-H activation; Amination; Nitrogen heterocycles; Palladium; Sulfur heterocycles
Categories
Funding
- Ministero dell'Universita e della Ricerca (MIUR) [PRIN 20154X9ATP]
- University of Milano
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In the presence of carbon monoxide, the palladium/phenanthroline system catalyzes the intramolecular amination of thiophene rings following the reduction of a nitroalkene moiety directly attached to the S-heterocyclic ring. Optimization of the ligand and reaction conditions allowed the synthesis of a series of thienopyrroles aryl/ alkyl-substituted at either the 2- or 3-position of the pyrrole ring. By using low pressures of carbon monoxide (5 bars), high yields of fused bicyclic compounds have been obtained (up to 98 % yield).
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