1,10-Phenanthroline- or Electron-Promoted Cyanation of Aryl Iodides

Published as part of the Cluster Electrochemical Synthesis and Catalysis

Abstract

A 1,10-phenanthroline-promoted cyanation of aryl iodides has been developed. 1,10-Phenanthroline worked as an organocatalyst for the reaction of aryl iodides with tetraalkylammonium cyanide to afford aryl cyanides. A similar reaction occurred through an electroreductive process.

Key words

cyanation - organocatalysis - electrochemistry - aryl iodides - aryl cyanides

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• 13 1-Naphthonitrile (2a); Typical ProcedureA solution of 1-iodonaphthalene (127 mg, 0.50 mmol), Et₄NCN (391 mg, 2.50 mmol), and 1,10-phenanthroline (18.2 mg, 0.1 mmol) in DMSO (1 mL) was stirred at 130 °C for 1 h. H₂O (15 mL) was added and the resulting mixture was extracted with EtOAc (3 × 5 mL). The combined organic phase was dried (MgSO₄), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, hexane–EtOAc (30:1)] to give a yellow oil; yield: 59.5 mg (0.39 mmol, 78%).IR (neat): 3061, 2222, 1591, 1512, 1375 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.53 (t, J = 7.8 Hz, 1 H), 7.63 (t, J = 7.6 Hz, 1 H), 7.70 (t, J = 7.9 Hz, 1 H), 7.87–7.96 (m, 2 H), 8.08 (d, J = 7.9 Hz, 1 H), 8.24 (d, J = 7.9 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 110.0, 117.7, 124.8, 125.0, 127.4, 128.5, 128.6, 132.2, 132.5, 132.8, 133.2.