Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

Keiichiro Iizumi; Miki B. Kurosawa; Ryota Isshiki; Kei Muto; Junichiro Yamaguchi

doi:10.1055/s-0040-1705943

Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

Keiichiro Iizumi, Miki B. Kurosawa, Ryota Isshiki, Kei Muto, Junichiro Yamaguchi^*

^*Corresponding author for this work

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

11 Citations (Scopus)

Abstract

A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.

Original language	English
Article number	st-2020-k0464-c
Pages (from-to)	1555-1559
Number of pages	5
Journal	Synlett
Volume	32
Issue number	15
DOIs	https://doi.org/10.1055/s-0040-1705943
Publication status	Published - 2021 Sept 16

Keywords

aminoacetonitriles
aromatic esters
coupling reaction
cyanation
nickel catalysis

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0040-1705943

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title = "Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst",

abstract = "A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.",

keywords = "aminoacetonitriles, aromatic esters, coupling reaction, cyanation, nickel catalysis",

author = "Keiichiro Iizumi and Kurosawa, {Miki B.} and Ryota Isshiki and Kei Muto and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number JP19H02726 (to J.Y.), JP20H04829 (hybrid catalysis), and JP19K15573 (to K.M.).JapanSocieyforhePromotionofScience(JP19H02726)JapanSocietyfrthePomoionofScience(JP19K15573) Publisher Copyright: {\textcopyright} 2020. Thieme. All rights reserved.",

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doi = "10.1055/s-0040-1705943",

language = "English",

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AU - Iizumi, Keiichiro

AU - Kurosawa, Miki B.

AU - Isshiki, Ryota

AU - Muto, Kei

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number JP19H02726 (to J.Y.), JP20H04829 (hybrid catalysis), and JP19K15573 (to K.M.).JapanSocieyforhePromotionofScience(JP19H02726)JapanSocietyfrthePomoionofScience(JP19K15573) Publisher Copyright: © 2020. Thieme. All rights reserved.

PY - 2021/9/16

Y1 - 2021/9/16

N2 - A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.

AB - A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.

KW - aminoacetonitriles

KW - aromatic esters

KW - coupling reaction

KW - cyanation

KW - nickel catalysis

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ER -

Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

Abstract

Keywords

ASJC Scopus subject areas

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