Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains

Xiangqian Liu; Jiaqi Jia; Magnus Rueping

doi:10.1021/acscatal.7b00941

Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains

Xiangqian Liu, Jiaqi Jia, Magnus Rueping

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

84 Scopus citations

Abstract

Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C–O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.

Original language	English (US)
Pages (from-to)	4491-4496
Number of pages	6
Journal	ACS Catalysis
Volume	7
Issue number	7
DOIs	https://doi.org/10.1021/acscatal.7b00941
State	Published - Jun 7 2017

Bibliographical note

KAUST Repository Item: Exported on 2018-05-17
Acknowledgements: X.L. was supported by the China Scholarship Council.

Keywords

alkylation
C-O activation
cross-coupling
decarbonylation
nickel catalysis

ASJC Scopus subject areas

Catalysis

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10.1021/acscatal.7b00941

http://repository.kaust.edu.sa/kaust/bitstream/10754/625106/1/Manuscript_revised.pdf

Cite this

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title = "Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains",

abstract = "Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C–O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.",

keywords = "alkylation, C-O activation, cross-coupling, decarbonylation, nickel catalysis",

author = "Xiangqian Liu and Jiaqi Jia and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2018-05-17 Acknowledgements: X.L. was supported by the China Scholarship Council.",

year = "2017",

month = jun,

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doi = "10.1021/acscatal.7b00941",

language = "English (US)",

volume = "7",

pages = "4491--4496",

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T1 - Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains

AU - Liu, Xiangqian

AU - Jia, Jiaqi

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2018-05-17 Acknowledgements: X.L. was supported by the China Scholarship Council.

PY - 2017/6/7

Y1 - 2017/6/7

N2 - Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C–O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.

AB - Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C–O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.

KW - alkylation

KW - C-O activation

KW - cross-coupling

KW - decarbonylation

KW - nickel catalysis

UR - http://hdl.handle.net/10754/625106

UR - http://pubs.acs.org/doi/full/10.1021/acscatal.7b00941

U2 - 10.1021/acscatal.7b00941

DO - 10.1021/acscatal.7b00941

M3 - Article

SN - 2155-5435

VL - 7

SP - 4491

EP - 4496

JO - ACS Catalysis

JF - ACS Catalysis

IS - 7

ER -

Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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