Suzuki reaction

In organic chemistry, the Suzuki reaction couples the following two things:

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• Organoborane, boronic acid or boronate ester 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 such as tetrakis(triphenylphosphine)palladium(0) to effect part of the transformation. The palladium catalyst (more strictly a pre-catalyst) is 4-coordinate, and usually involves phosphine supporting groups.

Related Topics:
1979 - Palladium - Catalyst - Tetrakis(triphenylphosphine)palladium(0) - Pre-catalyst - Phosphine

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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.

Related Topics:
Reductive elimination - Bond

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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.

Related Topics:
Triflates - Halides

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