C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes

Fang Jie Guo; Jing Sun; Zhao Qing Xu; Fritz E. Kühn; Shu Liang Zang; Ming Dong Zhou

doi:10.1016/j.catcom.2017.02.007

C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes

Fang Jie Guo, Jing Sun, Zhao Qing Xu, Fritz E. Kühn, Shu Liang Zang, Ming Dong Zhou

Associate Professorship of Molecular Catalysis

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

29 Scopus citations

Abstract

The C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated Ni (II) N-heterocyclic carbene (NHC) complexes is investigated. Good to excellent yields can be obtained for a variety of aryl halides when using 5 mol% of the Ni (II)-NHC catalyst and 1.5 eq. of KO^tBu. Both the electronic and steric effects of the NHC ligands on the catalytic performance of Ni (II)-NHC, as well as the electronic effects of aryl halides on coupling reactivity are examined. The mechanism for Ni (II)-NHC catalyzed coupling reactions is also discussed.

Original language	English
Pages (from-to)	11-14
Number of pages	4
Journal	Catalysis Communications
Volume	96
DOIs	https://doi.org/10.1016/j.catcom.2017.02.007
State	Published - 2017

Keywords

Aryl sulfides
C-S cross coupling
N-heterocyclic carbene
Nickel catalysis

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10.1016/j.catcom.2017.02.007

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title = "C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes",

abstract = "The C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated Ni (II) N-heterocyclic carbene (NHC) complexes is investigated. Good to excellent yields can be obtained for a variety of aryl halides when using 5 mol% of the Ni (II)-NHC catalyst and 1.5 eq. of KOtBu. Both the electronic and steric effects of the NHC ligands on the catalytic performance of Ni (II)-NHC, as well as the electronic effects of aryl halides on coupling reactivity are examined. The mechanism for Ni (II)-NHC catalyzed coupling reactions is also discussed.",

keywords = "Aryl sulfides, C-S cross coupling, N-heterocyclic carbene, Nickel catalysis",

author = "Guo, {Fang Jie} and Jing Sun and Xu, {Zhao Qing} and K{\"u}hn, {Fritz E.} and Zang, {Shu Liang} and Zhou, {Ming Dong}",

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year = "2017",

doi = "10.1016/j.catcom.2017.02.007",

language = "English",

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journal = "Catalysis Communications",

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T1 - C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes

AU - Guo, Fang Jie

AU - Sun, Jing

AU - Xu, Zhao Qing

AU - Kühn, Fritz E.

AU - Zang, Shu Liang

AU - Zhou, Ming Dong

PY - 2017

Y1 - 2017

N2 - The C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated Ni (II) N-heterocyclic carbene (NHC) complexes is investigated. Good to excellent yields can be obtained for a variety of aryl halides when using 5 mol% of the Ni (II)-NHC catalyst and 1.5 eq. of KOtBu. Both the electronic and steric effects of the NHC ligands on the catalytic performance of Ni (II)-NHC, as well as the electronic effects of aryl halides on coupling reactivity are examined. The mechanism for Ni (II)-NHC catalyzed coupling reactions is also discussed.

AB - The C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated Ni (II) N-heterocyclic carbene (NHC) complexes is investigated. Good to excellent yields can be obtained for a variety of aryl halides when using 5 mol% of the Ni (II)-NHC catalyst and 1.5 eq. of KOtBu. Both the electronic and steric effects of the NHC ligands on the catalytic performance of Ni (II)-NHC, as well as the electronic effects of aryl halides on coupling reactivity are examined. The mechanism for Ni (II)-NHC catalyzed coupling reactions is also discussed.

KW - Aryl sulfides

KW - C-S cross coupling

KW - N-heterocyclic carbene

KW - Nickel catalysis

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DO - 10.1016/j.catcom.2017.02.007

M3 - Article

AN - SCOPUS:85015798090

SN - 1566-7367

VL - 96

SP - 11

EP - 14

JO - Catalysis Communications

JF - Catalysis Communications

ER -

C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes

Abstract

Keywords

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