Hirao coupling explained

The Hirao coupling (also called the Hirao reaction or the Hirao cross-coupling) is the chemical reaction involving the palladium-catalyzed cross-coupling of a dialkyl phosphite and an aryl halide to form a phosphonate.[1] [2] [3] This reaction is named after Toshikazu Hirao and is related to the Michaelis-Arbuzov reaction. In contrast to the classic Michaelis-Arbuzov reaction, which is limited to alkyl phosphonates, the Hirao coupling can also deliver aryl phosphonates.

References

  1. Toshikazu . Hirao . Toshio . Masunaga . Yoshiki . Ohshiro . Toshio . Agawa . A Novel Synthesis of Dialkyl Arenephosphonates . . 1981 . 1981 . 1 . 56–57 . 10.1055/s-1981-29335.
  2. Y. . Belabassi . S. . Alzghari . J.L. . Montchamp . Revisiting the Hirao Cross-coupling: Improved Synthesis of Aryl and Heteroaryl Phosphonates . . 15 January 2008 . 693 . 19 . 3171–3178 . 19156189 . 2587344 . 10.1016/j.jorganchem.2008.07.020.
  3. Mark C. . Kohler . Joseph G. . Sokol . Robert A. . Stockland Jr. . Development of a room temperature Hirao reaction . . 50 . 4 . 457–459 . 28 January 2009 . 10.1016/j.tetlet.2008.11.040.

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