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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.


ABSTRACT: We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)6](BF4)2, 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si-Me4-DHP). Si-Me4-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.

SUBMITTER: Ueda Y 

PROVIDER: S-EPMC6349056 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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

Ueda Yohei Y   Tsujimoto Nagataka N   Yurino Taiga T   Tsurugi Hayato H   Mashima Kazushi K  

Chemical science 20181126 4


We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)<sub>6</sub>](BF<sub>4</sub>)<sub>2</sub>, 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (<i>Si</i>-Me<sub>4</sub>-DHP). <i>Si</i>-Me<sub>4</sub>-DHP was found to function as a reductant for generating nickel(0) species and a silylation reagent to achieve the catalytic cyanation <i>via</i> C-CN bond cleavage. ...[more]

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