Hirao coupling

Hirao coupling
Named after	Toshikazu Hirao
Reaction type	Coupling reaction

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

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

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[1] Hirao, Toshikazu; Masunaga, Toshio; Ohshiro, Yoshiki; Agawa, Toshio (1981). "A Novel Synthesis of Dialkyl Arenephosphonates". Synthesis. 1981 (1): 56–57. doi:10.1055/s-1981-29335.

[2] Belabassi, Y.; Alzghari, S.; Montchamp, J.L. (15 January 2008). "Revisiting the Hirao Cross-coupling: Improved Synthesis of Aryl and Heteroaryl Phosphonates". J. Organomet. Chem. 693 (19): 3171–3178. doi:10.1016/j.jorganchem.2008.07.020. PMC 2587344. PMID 19156189.

[3] Kohler, Mark C.; Sokol, Joseph G.; Stockland Jr., Robert A. (28 January 2009). "Development of a room temperature Hirao reaction". Tetrahedron Letters. 50 (4): 457–459. doi:10.1016/j.tetlet.2008.11.040.

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