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...

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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
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author Ueda, Yohei
Tsujimoto, Nagataka
Yurino, Taiga
Tsurugi, Hayato
Mashima, Kazushi
author_facet Ueda, Yohei
Tsujimoto, Nagataka
Yurino, Taiga
Tsurugi, Hayato
Mashima, Kazushi
author_sort Ueda, Yohei
collection PubMed
description 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.
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spelling pubmed-63490562019-02-15 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 Ueda, Yohei Tsujimoto, Nagataka Yurino, Taiga Tsurugi, Hayato Mashima, Kazushi Chem Sci Chemistry 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. Royal Society of Chemistry 2018-11-26 /pmc/articles/PMC6349056/ /pubmed/30774893 http://dx.doi.org/10.1039/c8sc04437f Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Ueda, Yohei
Tsujimoto, Nagataka
Yurino, Taiga
Tsurugi, Hayato
Mashima, Kazushi
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349056/
https://www.ncbi.nlm.nih.gov/pubmed/30774893
http://dx.doi.org/10.1039/c8sc04437f
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