Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile via C–CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine

We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)(6)](BF(4))(2), 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si–Me(4)-DHP). Si–Me(4)-DHP was found to function as a reduc...

Descripción completa

Detalles Bibliográficos
Autores principales: Ueda, Yohei, Tsujimoto, Nagataka, Yurino, Taiga, Tsurugi, Hayato, Mashima, Kazushi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349056/
https://www.ncbi.nlm.nih.gov/pubmed/30774893
http://dx.doi.org/10.1039/c8sc04437f
Descripción
Sumario:We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)(6)](BF(4))(2), 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si–Me(4)-DHP). Si–Me(4)-DHP was found to function as a reductant for generating nickel(0) species and a silylation reagent to achieve the catalytic cyanation via C–CN bond cleavage.

Ejemplares similares