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The coupling reaction of pinacolborane with various aryl bromides in the presence of a catalytic amount of Pd(OAc)(2) together with DPEphos as ligand and Et(3)N as base provided arylboronates. High yields were obtained in the case of electron-donor substituted aryl bromides. The direct preparation of arylboronates allowed the one-pot, two-step synthesis of unsymmetrical biaryls in high yields. [reaction: see text]

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[reaction: see text] Highly diastereoselective biaryl Suzuki coupling reactions of (1R)-1-(2-iodo or bromophenyl)-2-(R)-(4-tolylsulfinyl)-1-ethanol derivatives with various aryl- or naphthylboronic acids (or esters) were performed with high yields (up to 99%) and an excellent control of the axial chirality (up to 98% de).

Asymmetric biaryl Suzuki coupling reactions were performed with various aryl‐ or naphthylhalide‐bearing enantiomerically pure benzylic alcohols and aryl‐ or naphthylboronic acids (or esters). The stereogenic benzylic alcohol was introduced by diastereoselective reduction of the arylhalide bearing a β‐keto sulfoxide. In the presence of Pd(OAc)2/CsF and dppf or PPh3 excellent yields and atropodiastereoselectivities were obtained. The absolute configurations of the biaryls were determined by X‐ray crystallography and 1H NMR NOESY experiments. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)