Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

Huifeng Yue; Chen Zhu; Li Shen; Qiuyang Geng; Katharina J. Hock; Tingting Yuan; Luigi Cavallo; Magnus Rueping

doi:10.1039/c9sc00783k

Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

Huifeng Yue, Chen Zhu, Li Shen, Qiuyang Geng, Katharina J. Hock, Tingting Yuan, Luigi Cavallo, Magnus Rueping

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138 Scopus citations

Abstract

Nickel-catalyzed reductive cross coupling of activated primary amines with aryl halides under mild reaction conditions has been achieved for the first time. Due to the avoidance of stoichiometric organometallic reagents and external bases, the scope regarding both coupling partners is broad. Thus, a wide range of substrates, natural products and drugs with diverse functional groups are tolerated. Moreover, experimental mechanistic investigations and density functional theory (DFT) calculations in combination with wavefunction analysis have been performed to understand the catalytic cycle in more detail.

Original language	English (US)
Pages (from-to)	4430-4435
Number of pages	6
Journal	Chemical Science
Volume	10
Issue number	16
DOIs	https://doi.org/10.1039/c9sc00783k
State	Published - 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: H. Y. acknowledges the China Scholarship Council. C. Z. acknowledges the King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.

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Cite this

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title = "Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling",

abstract = "Nickel-catalyzed reductive cross coupling of activated primary amines with aryl halides under mild reaction conditions has been achieved for the first time. Due to the avoidance of stoichiometric organometallic reagents and external bases, the scope regarding both coupling partners is broad. Thus, a wide range of substrates, natural products and drugs with diverse functional groups are tolerated. Moreover, experimental mechanistic investigations and density functional theory (DFT) calculations in combination with wavefunction analysis have been performed to understand the catalytic cycle in more detail.",

author = "Huifeng Yue and Chen Zhu and Li Shen and Qiuyang Geng and Hock, {Katharina J.} and Tingting Yuan and Luigi Cavallo and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: H. Y. acknowledges the China Scholarship Council. C. Z. acknowledges the King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.",

year = "2019",

doi = "10.1039/c9sc00783k",

language = "English (US)",

volume = "10",

pages = "4430--4435",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "16",

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TY - JOUR

T1 - Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

AU - Yue, Huifeng

AU - Zhu, Chen

AU - Shen, Li

AU - Geng, Qiuyang

AU - Hock, Katharina J.

AU - Yuan, Tingting

AU - Cavallo, Luigi

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: H. Y. acknowledges the China Scholarship Council. C. Z. acknowledges the King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.

PY - 2019

Y1 - 2019

N2 - Nickel-catalyzed reductive cross coupling of activated primary amines with aryl halides under mild reaction conditions has been achieved for the first time. Due to the avoidance of stoichiometric organometallic reagents and external bases, the scope regarding both coupling partners is broad. Thus, a wide range of substrates, natural products and drugs with diverse functional groups are tolerated. Moreover, experimental mechanistic investigations and density functional theory (DFT) calculations in combination with wavefunction analysis have been performed to understand the catalytic cycle in more detail.

AB - Nickel-catalyzed reductive cross coupling of activated primary amines with aryl halides under mild reaction conditions has been achieved for the first time. Due to the avoidance of stoichiometric organometallic reagents and external bases, the scope regarding both coupling partners is broad. Thus, a wide range of substrates, natural products and drugs with diverse functional groups are tolerated. Moreover, experimental mechanistic investigations and density functional theory (DFT) calculations in combination with wavefunction analysis have been performed to understand the catalytic cycle in more detail.

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UR - https://pubs.rsc.org/en/Content/ArticleLanding/2019/SC/C9SC00783K#!divAbstract

UR - http://www.scopus.com/inward/record.url?scp=85064704683&partnerID=8YFLogxK

U2 - 10.1039/c9sc00783k

DO - 10.1039/c9sc00783k

M3 - Article

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SN - 2041-6520

VL - 10

SP - 4430

EP - 4435

JO - Chemical Science

JF - Chemical Science

IS - 16

ER -

Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

Abstract

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