Copper-promoted carbon-nitrogen bond formation with 2-iodo-selenophene and amides.
We present here carbon-nitrogen bond formation via a coupling reaction of 2-iodo-selenophene catalyzed by Cu(I) in the presence of a base and an inexpensive ligand, and establish the first route to obtaining 2-nitrogen-selenophene derivatives in good yields. We can anticipate that this reaction works well with oxazolidinones, lactams, and aliphatic and aromatic amides, as nitrogen sources, in the absence of any supplementary additives. In addition, the reaction proceeded cleanly under mild reaction conditions and was sensitive to the ratio of amide/2-iodo-selenophene, as well as the nature of the ligand, base, and solvent.
Soares do Rêgo Barros
Olga
O
Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, Rio Grande do Sul, Brazil 97105-900.
Nogueira
Cristina W
CW
Stangherlin
Eluza C
EC
Menezes
Paulo Henrique
PH
Zeni
Gilson
G
D000577:Amides; D002244:Carbon; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007455:Iodine; D008024:Ligands; D009584:Nitrogen; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents
D000577:Amides; D008024:Ligands; D016566:Organoselenium Compounds; D012997:Solvents; D002244:Carbon; D003300:Copper; D007455:Iodine; D009584:Nitrogen