Novel and Efficient Synthesis of Symmetrical Functionalized Biaryls Using Zinc and Triethylammonium Formate

Abstract

Reductive homocoupling of aryl halides in the presence of commercial zinc dust and triethylammonium formate in methanol produces biaryls in good to excellent yields. Aryl halides having either electron-donating or electron-withdrawing groups underwent smooth coupling to afford the corresponding symmetrical biaryls. The reductive coupling did not occur without triethylammonium formate. Addition of one equivalent of sodium hydroxide enhanced the coupling reaction rate. The commercial zinc dust is inexpensive, widely available and can be used without any auxiliary catalysts such as Pd(0) and/or Ni(0).

Key words

aryl halides - homocoupling - zinc - triethylammonium formate - biaryls

References

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17

For zinc/nickel catalyst-promoted reaction, reductive elimination of Ar₂Ni affording Ar₂ was proposed as a plausible mechanism. [11]

18

The spectra were compared to those of a commercial sample.