In
cross-coupling reaction
In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important re ...
s, the component reagents are called cross-coupling partners or simply coupling partners. These reagents can be further classified according to their
nucleophilic
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they a ...
vs
electrophilic
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carr ...
character:
:R-X + R'-Y → R-R' + XY
Typically the electrophilic coupling partner (R-X) is an aryl halide, but triflates are also used. Nucleophilic coupling (R'-Y) partners are more diverse. In the
Suzuki reaction
The Suzuki reaction or Suzuki coupling is an organic reaction that uses a palladium complex catalyst to cross-couple a boronic acid to an organohalide. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemi ...
,
boronic esters and
boronic acid
A boronic acid is an organic compound related to boric acid () in which one of the three hydroxyl groups () is replaced by an alkyl or aryl group (represented by R in the general formula ). As a compound containing a carbon–boron bond, memb ...
s serve as nucleophilic coupling partners. Expanding the scope of coupling partners is a focus methods development in
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
.
[{{cite journal , title=4-Methoxy-4'-nitrophenyl. Recent Advances In The Stille Biaryl Coupling Reaction and Applications in Complex Natural Products Synthesis, doi=10.15227/orgsyn.088.0197, author=Robert M. Williams, journal=Org. Synth., year=2011, volume=88, pages=197–201 , pmid=21960729 , pmc=3181114 ]
References
Carbon-carbon bond forming reactions