Photoinduced Nickel-Catalyzed Demethylative Cyanation and Decarboxylative Cyanomethylation of Aryl Halides

Shao Chi Lee; Chen Zhu; Kun Huang; Jeremy A. Bau; Jiaqi Jia; Huifeng Yue; Magnus Rueping

doi:10.1021/acscatal.3c04745

Photoinduced Nickel-Catalyzed Demethylative Cyanation and Decarboxylative Cyanomethylation of Aryl Halides

Shao Chi Lee^*, Chen Zhu^*, Kun Huang, Jeremy A. Bau, Jiaqi Jia, Huifeng Yue^*, Magnus Rueping^*

^*Corresponding author for this work

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

5 Scopus citations

Abstract

Photoinduced nickel-catalyzed demethylative cyanation and decarboxylative cyanomethylation of aryl halides are described here. Commercially available bromoacetonitrile was found to act as an efficient cyanating reagent for the photoinduced cyanation reaction in the absence of a photocatalyst. Moreover, photoredox and nickel dual-catalyzed decarboxylative cyanomethylation of aryl halides has also been realized using cesium cyanoacetate under mild conditions. A series of aryl and benzyl nitriles bearing diverse functional groups were prepared with good to high efficiency.

Original language	English (US)
Pages (from-to)	16279-16285
Number of pages	7
Journal	ACS Catalysis
Volume	13
Issue number	24
DOIs	https://doi.org/10.1021/acscatal.3c04745
State	Published - Dec 15 2023

Keywords

aryl halides
cyanation
cyanomethylation
nickel
photocatalysis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1021/acscatal.3c04745

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title = "Photoinduced Nickel-Catalyzed Demethylative Cyanation and Decarboxylative Cyanomethylation of Aryl Halides",

abstract = "Photoinduced nickel-catalyzed demethylative cyanation and decarboxylative cyanomethylation of aryl halides are described here. Commercially available bromoacetonitrile was found to act as an efficient cyanating reagent for the photoinduced cyanation reaction in the absence of a photocatalyst. Moreover, photoredox and nickel dual-catalyzed decarboxylative cyanomethylation of aryl halides has also been realized using cesium cyanoacetate under mild conditions. A series of aryl and benzyl nitriles bearing diverse functional groups were prepared with good to high efficiency.",

keywords = "aryl halides, cyanation, cyanomethylation, nickel, photocatalysis",

author = "Lee, {Shao Chi} and Chen Zhu and Kun Huang and Bau, {Jeremy A.} and Jiaqi Jia and Huifeng Yue and Magnus Rueping",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = dec,

day = "15",

doi = "10.1021/acscatal.3c04745",

language = "English (US)",

volume = "13",

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journal = "ACS Catalysis",

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number = "24",

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TY - JOUR

T1 - Photoinduced Nickel-Catalyzed Demethylative Cyanation and Decarboxylative Cyanomethylation of Aryl Halides

AU - Lee, Shao Chi

AU - Zhu, Chen

AU - Huang, Kun

AU - Bau, Jeremy A.

AU - Jia, Jiaqi

AU - Yue, Huifeng

AU - Rueping, Magnus

PY - 2023/12/15

Y1 - 2023/12/15

N2 - Photoinduced nickel-catalyzed demethylative cyanation and decarboxylative cyanomethylation of aryl halides are described here. Commercially available bromoacetonitrile was found to act as an efficient cyanating reagent for the photoinduced cyanation reaction in the absence of a photocatalyst. Moreover, photoredox and nickel dual-catalyzed decarboxylative cyanomethylation of aryl halides has also been realized using cesium cyanoacetate under mild conditions. A series of aryl and benzyl nitriles bearing diverse functional groups were prepared with good to high efficiency.

AB - Photoinduced nickel-catalyzed demethylative cyanation and decarboxylative cyanomethylation of aryl halides are described here. Commercially available bromoacetonitrile was found to act as an efficient cyanating reagent for the photoinduced cyanation reaction in the absence of a photocatalyst. Moreover, photoredox and nickel dual-catalyzed decarboxylative cyanomethylation of aryl halides has also been realized using cesium cyanoacetate under mild conditions. A series of aryl and benzyl nitriles bearing diverse functional groups were prepared with good to high efficiency.

KW - aryl halides

KW - cyanation

KW - cyanomethylation

KW - nickel

KW - photocatalysis

UR - http://www.scopus.com/inward/record.url?scp=85180087638&partnerID=8YFLogxK

U2 - 10.1021/acscatal.3c04745

DO - 10.1021/acscatal.3c04745

M3 - Article

AN - SCOPUS:85180087638

SN - 2155-5435

VL - 13

SP - 16279

EP - 16285

JO - ACS Catalysis

JF - ACS Catalysis

IS - 24

ER -

Photoinduced Nickel-Catalyzed Demethylative Cyanation and Decarboxylative Cyanomethylation of Aryl Halides

Abstract

Keywords

ASJC Scopus subject areas

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