CHEMISTRY: Catalytic Coupling

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Science  09 Apr 2004:
Vol. 304, Issue 5668, pp. 173a
DOI: 10.1126/science.304.5668.173a

One of the most useful tools for forming carbon-carbon bonds is the Suzuki-Miyaura coupling, in which compounds such as aryl halides are cross-coupled to organoboronic acids, in part because the boronic acids are readily handled in air or water without special precautions. However, steric hindrance around the carbon atoms is not always tolerated, and catalyst loadings or reaction temperature or both may need to be high. Walker et al. have designed a new Pd ligand (1) bearing methoxy groups that not only stabilize the Pd complex but also avoid the deactivating effect of cyclometalation. They report yields in excess of 95% for a wide variety of couplings, including hindered and heteroatom halide substrates at temperatures near 100°C and unhindered substrates at room temperature. In many cases, Pd loadings of well below 0.1 mole % suffice for efficient catalysis. — PDS

Angew. Chem. Int. Ed. 43, 1871 (2004).

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