Suzuki reaction
From Biocrawler, the free encyclopedia.
In organic chemistry, the Suzuki reaction couples the following two things:
- Organoborane, in a basic solution
- An aryl, benzyl, or vinyl halide
First published in 1979 by Suzuki, the Suzuki reaction couples boronic acids (containing an orangic part) to halides. The reaction relies on a palladium catalyst to effect part of the transformation. The palladium catalyst is 4-coordinate, and usually involves phosphine supporting groups.
An example reaction is given as a diagram on this page at right. The reaction proceeds first by reaction of the organohalide with the palladium(0) complex to give a palladium(II) intermediate. The Pd(II) complex then undergoes transmetallation with the base-activated boronic acid (activation adds an OH or otherwise negatively charged group (e.g. OEt), causing the B to become negatively charged, expelling the alkenyl group onto the Pd). Reductive elimination follows to give the cross-coupled product, with the new bond shown in red in the figure.
It should also be noted that the reaction works with triflates (OTf) instead of halides, and also with boron-esters instead of boronic acids. There has been much interest in this relatively recent discovery and much work on derivatizing the original reaction has been done with much success.
External link
Article about the Suzuki reaction (http://www.chemicals.matthey.com/catalysts/viewnarrative.asp?processid=105&structure=True&catalyst=True)
