The Fukuyama coupling is a
coupling reaction A coupling reaction in organic chemistry is a general term for a variety of reactions where two fragments are joined together with the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (R = ...
taking place between a
thioester
In organic chemistry, thioesters are organosulfur compounds with the functional group . They are analogous to carboxylate esters () with the sulfur in the thioester playing the role of the linking oxygen in the carboxylate ester, as implied by t ...
and an
organozinc halide in the presence of a
palladium
Palladium is a chemical element with the symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1803 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas, which was itself na ...
catalyst. The reaction product is a
ketone. This reaction was discovered by
Tohru Fukuyama et al. in 1998. Advantages are high chemoselectivity, mild reaction conditions and the use of less-toxic reagents.
:
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
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
such as ketones, acetates, sulfides, aromatic bromides, chlorides and aldehydes.
:
The reaction (interrupted) has been used in the synthesis of
biotin
:
This reaction was preceded by the conceptually related
Fukuyama reduction.
References
{{Reflist
Carbon-carbon bond forming reactions
Name reactions