Ni(i)-Ni(iii) cycle in Buchwald-Hartwig amination of aryl bromide mediated by NHC-ligated Ni(i) complexes

Takahiro Inatomi; Yukino Fukahori; Yuji Yamada; Ryuta Ishikawa; Shinji Kanegawa; Yuji Koga; Kouki Matsubara

doi:10.1039/c8cy02427h

Ni(i)-Ni(iii) cycle in Buchwald-Hartwig amination of aryl bromide mediated by NHC-ligated Ni(i) complexes

Takahiro Inatomi, Yukino Fukahori, Yuji Yamada, Ryuta Ishikawa, Shinji Kanegawa, Yuji Koga, Kouki Matsubara

Department of Fundamental Organic Chemistry

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

Intermediate amide complexes of NHC-ligated monovalent nickel in Buchwald-Hartwig amination of aryl halides were isolated and structurally characterized. The amide complexes reacted with aryl bromide to form a cross-coupling product. Lowerature observation of the oxidative addition product of the Ni(i) amide complex with aryl bromide indicated the presence of a Ni(iii) intermediate. The results showed that a well-defined mononuclear NHC-Ni(i) complex can act as a key intermediate in homogeneous catalysis.

Original language	English
Pages (from-to)	1784-1793
Number of pages	10
Journal	Catalysis Science and Technology
Volume	9
Issue number	8
DOIs	https://doi.org/10.1039/c8cy02427h
Publication status	Published - 2019

All Science Journal Classification (ASJC) codes

Catalysis

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10.1039/c8cy02427h

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title = "Ni(i)-Ni(iii) cycle in Buchwald-Hartwig amination of aryl bromide mediated by NHC-ligated Ni(i) complexes",

abstract = "Intermediate amide complexes of NHC-ligated monovalent nickel in Buchwald-Hartwig amination of aryl halides were isolated and structurally characterized. The amide complexes reacted with aryl bromide to form a cross-coupling product. Lowerature observation of the oxidative addition product of the Ni(i) amide complex with aryl bromide indicated the presence of a Ni(iii) intermediate. The results showed that a well-defined mononuclear NHC-Ni(i) complex can act as a key intermediate in homogeneous catalysis.",

author = "Takahiro Inatomi and Yukino Fukahori and Yuji Yamada and Ryuta Ishikawa and Shinji Kanegawa and Yuji Koga and Kouki Matsubara",

note = "Funding Information: This work was supported by the Japan Society for the Promotion of Science (Grant-in-Aid for Scientific Research 22550104 and 25410123). Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",

year = "2019",

doi = "10.1039/c8cy02427h",

language = "English",

volume = "9",

pages = "1784--1793",

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TY - JOUR

T1 - Ni(i)-Ni(iii) cycle in Buchwald-Hartwig amination of aryl bromide mediated by NHC-ligated Ni(i) complexes

AU - Inatomi, Takahiro

AU - Fukahori, Yukino

AU - Yamada, Yuji

AU - Ishikawa, Ryuta

AU - Kanegawa, Shinji

AU - Koga, Yuji

AU - Matsubara, Kouki

N1 - Funding Information: This work was supported by the Japan Society for the Promotion of Science (Grant-in-Aid for Scientific Research 22550104 and 25410123). Publisher Copyright: © 2019 The Royal Society of Chemistry. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

PY - 2019

Y1 - 2019

N2 - Intermediate amide complexes of NHC-ligated monovalent nickel in Buchwald-Hartwig amination of aryl halides were isolated and structurally characterized. The amide complexes reacted with aryl bromide to form a cross-coupling product. Lowerature observation of the oxidative addition product of the Ni(i) amide complex with aryl bromide indicated the presence of a Ni(iii) intermediate. The results showed that a well-defined mononuclear NHC-Ni(i) complex can act as a key intermediate in homogeneous catalysis.

AB - Intermediate amide complexes of NHC-ligated monovalent nickel in Buchwald-Hartwig amination of aryl halides were isolated and structurally characterized. The amide complexes reacted with aryl bromide to form a cross-coupling product. Lowerature observation of the oxidative addition product of the Ni(i) amide complex with aryl bromide indicated the presence of a Ni(iii) intermediate. The results showed that a well-defined mononuclear NHC-Ni(i) complex can act as a key intermediate in homogeneous catalysis.

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DO - 10.1039/c8cy02427h

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ER -

Ni(i)-Ni(iii) cycle in Buchwald-Hartwig amination of aryl bromide mediated by NHC-ligated Ni(i) complexes

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