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Copper‐Catalyzed Carbon‐Nitrogen/Carbon‐Selenium Bonds Formation: Synthesis of 2‐(Organochalcogenyl)‐indolizines
Author(s) -
Goulart Tales A. C.,
Back Davi F.,
Zeni Gilson
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700166
Subject(s) - chemistry , indolizine , catalysis , copper , iodide , combinatorial chemistry , selenium , coupling reaction , organic chemistry
The copper‐catalyzed cyclization of propargylpyridines with diorganyl dichalcogenides was applied to the synthesis of 2‐(organochalcogenyl)‐indolizines. A systematic study of the cyclization system revealed that the mutual action between copper(I) iodide and diorganyl dichalcogenides is essential for the formation of indolizines in good yields avoiding the formation of hydrogenated indolizine. The standard reaction conditions were compatible with many functional groups in the substrates, such as methyl, chlorine, fluorine, methoxy and trifluoromethyl. This protocol was efficient with diorganyl diselenides and ditellurides but ineffective with diorganyl disulfides. In addition, the obtained 2‐(organochalcogenyl)‐indolizines were readily transformed into more complex products by reaction with boronic acids using palladium‐catalyzed cross‐coupling conditions.