In Situ Demethoxylation, Dechloridation, or Decyanogenation from Coupling Aromatic Compounds Mediated by Potassium Metal

Abstract

The potassium metal can promote direct arylation of unactivated aromatic C-H bonds under an oxygen atmosphere. Interestingly, in situ demethoxylation, dechloridation, or decyanogenation from the corresponding coupling aromatic compounds mediated by potassium metal was also observed in the radical reaction systems.

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GRAPHICAL ABSTRACT

Keywords:

• Biaryl
• C-H activation
• coupling reaction
• potassium metal
• radical reaction

ACKNOWLEDGMENT

This work was supported by the National Natural Science Foundation of China (No. 21172210 and 20872135).

Notes

^a Reaction was carried out under different atmosphere using iodo- or chloro-benzene (1: 1.5 mmol) and benzene (2: 20 mL, 225 mmol) in a three-necked flask.

^b Isolated yield based on 1.

^a The reaction was carried out under an oxygen atmosphere using aryl halide (1: 1.5 mmol) and benzene (2: 20 mL, 225 mmol) in a three-necked flask.

^b Isolated yield based on 1.

^c Possible by-product of KCN should be carefully treated!

^d Biphenyl (3a) was also produced in about 8% yield.