Synlett
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

Publication Date:
16 October 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
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  • 19 2-Naphthonitrile (3A); Typical Procedure A 20-mL glass vessel, equipped with a J. Young O-ring tap and a magnetic stirring bar, was charged with Ni(OAc)2·4 H2O (10.0 mg, 0.040 mmol, 10 mol%) and Na2CO3 (63.6 mg, 0.60 mmol, 1.5 equiv). The vessel was evacuated and its contents were dried with a heat gun. The vessel was then cooled to r.t., and filled with N2 gas. Phenyl 2-naphthoate (1A; 99.3 mg, 0.40 mmol, 1.0 equiv), 2-morpholinoacetonitrile (2a: 100.9 mg, 0.80 mmol, 2.0 equiv), and dcypt (38.1 mg, 0.080 mmol, 20 mol%) were added, and the vessel was evacuated and refilled with N2 gas three times. Toluene (1.6 mL) was added, and the vessel was sealed with the O-ring tap and heated at 160 °C in a nine-well reaction block for 24 h with stirring. The mixture was then cooled to r.t. and passed through a short silica-gel pad with EtOAc as an eluent. The filtrate was concentrated in vacuo, and the residue was purified by preparative TLC (hexane–EtOAc, 4:1) to give a white solid; yield: 46.3 mg (76%) (caution! The reaction should be conducted in a well-functioning fume hood to avoid exposure to the CO gas generated by the reaction. After the reaction, the vessel should be opened in the fume hood for the same reason.) 1H NMR (400 MHz, CDCl3): δ = 8.23 (s, 1 H), 7.93–7.87 (m, 3 H), 7.67–7.58 (m, 3 H). 13C NMR (101 MHz, CDCl3): δ = 134.6, 134.1, 132.2, 129.1, 129.0, 128.4, 128.0, 127.6, 126.3, 119.2, 109.3. HRMS (DART): m/z [M + NH4]+ calcd for C11H11N2: 171.0917; found: 171.0915.