Synlett 2021; 32(15): 1555-1559
DOI: 10.1055/s-0040-1705943
cluster
Modern Nickel-Catalyzed Reactions

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

Keiichiro Iizumi
a   Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan   Email: junyamaguchi@waseda.jp
,
Miki B. Kurosawa
a   Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan   Email: junyamaguchi@waseda.jp
,
Ryota Isshiki
a   Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan   Email: junyamaguchi@waseda.jp
,
Kei Muto
b   Institute for Advanced Study, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan
,
a   Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan   Email: junyamaguchi@waseda.jp
› Author Affiliations
This work was supported by JSPS KAKENHI Grant Number JP19H02726 (to J.Y.), JP20H04829 (hybrid catalysis), and JP19K15573 (to K.M.).


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.

Supporting Information



Publication History

Received: 24 August 2020

Accepted after revision: 17 September 2020

Article published online:
16 October 2020

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