Fukuyama coupling

Fukuyama coupling
Named after	Tohru Fukuyama
Reaction type	Coupling reaction
Identifiers
Organic Chemistry Portal	fukuyama-coupling

The Fukuyama coupling is a coupling reaction taking place between a thioester and an organozinc halide in the presence of a palladium catalyst. The reaction product is a ketone. This reaction was discovered by Tohru Fukuyama et al. in 1998.[1] Advantages are high chemoselectivity, mild reaction conditions and the use of less-toxic reagents.[2]

One advantage of this method is that the reaction stops at the ketone and does not proceed to a tertiary alcohol. In addition, the protocol is compatible with functional groups such as ketones, acetates, sulfides, aromatic bromides, chlorides and aldehydes.

The reaction (interrupted) has been used in the synthesis of biotin [3]

This reaction was preceded by the conceptually related Fukuyama reduction.

References

Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. (1998). "A novel ketone synthesis by a palladium-catalyzed reaction of thiol esters and organozinc reagents". Tetrahedron Letters. 39 (20): 3189–3192. doi:10.1016/S0040-4039(98)00456-0.
Mori, Y.; Seki, M. (2007). "SYNTHESIS OF MULTI-FUNCTIONALIZED KETONES THROUGH THE FUKUYAMA COUPLING REACTION CATALYZED BY PEARLMAN'S CATALYST: PREPARATION OF ETHYL 6-OXOTRIDECANOATE (Tridecanoic acid, 6-oxo-, ethyl ester)" (PDF). Organic Syntheses. 84: 285–294.CS1 maint: multiple names: authors list (link); Collective Volume, 11, pp. 281–288
Shimizu, T.; Seki, M. (2000). "Facile synthesis of (+)-biotin via Fukuyama coupling reaction". Tetrahedron Letters. 41 (26): 5099–5101. doi:10.1016/S0040-4039(00)00781-4.

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[1] Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. (1998). "A novel ketone synthesis by a palladium-catalyzed reaction of thiol esters and organozinc reagents". Tetrahedron Letters. 39 (20): 3189–3192. doi:10.1016/S0040-4039(98)00456-0.

[2] Mori, Y.; Seki, M. (2007). "SYNTHESIS OF MULTI-FUNCTIONALIZED KETONES THROUGH THE FUKUYAMA COUPLING REACTION CATALYZED BY PEARLMAN'S CATALYST: PREPARATION OF ETHYL 6-OXOTRIDECANOATE (Tridecanoic acid, 6-oxo-, ethyl ester)" (PDF). Organic Syntheses. 84: 285–294.CS1 maint: multiple names: authors list (link); Collective Volume, 11, pp. 281–288

[3] Shimizu, T.; Seki, M. (2000). "Facile synthesis of (+)-biotin via Fukuyama coupling reaction". Tetrahedron Letters. 41 (26): 5099–5101. doi:10.1016/S0040-4039(00)00781-4.