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

Synlett, Table of Contents

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

Authors

Keiichiro Iizumi

^aDepartment of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan Email: junyamaguchi@waseda.jp
Miki B. Kurosawa

^aDepartment of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan Email: junyamaguchi@waseda.jp
Ryota Isshiki

^aDepartment of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan Email: junyamaguchi@waseda.jp
Kei Muto

^bInstitute for Advanced Study, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan
Junichiro Yamaguchi ∗

^aDepartment of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan Email: junyamaguchi@waseda.jp

Abstract

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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.

Key words

nickel catalysis - cyanation - aromatic esters - aminoacetonitriles - coupling reaction

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References

References and Notes

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18 A main reason for the modest yield of some products was the decomposition of the phenyl esters to the corresponding carboxylic acids.
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.

Supplementary Material

Supporting Information (PDF)