Palladium-Catalyzed Cross-Coupling of Organoboron Compounds with Iodonium Salts and Iodanes.

Suk-Ku Kang, Hong-Woo Lee, Su-Bum Jang, Pil-Su Ho

Index: J. Org. Chem. 61 , 4720, (1996)

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Abstract

The palladium-catalyzed cross-coupling reaction of iodinanes (iodonium salts and iodanes) with organoboron compounds to form carbon-carbon bonds was achieved at ambient temperature under aqueous conditions in the absence of base. Coupling of phenylboronic acid with diphenyliodonium tetrafluoroborate in the presence of Pd(PPh(3))(4) (0.2 mol %) or Pd(OAc)(2) (0.2 mol %) under aqueous conditions gave biphenyl in almost quantitative yield. Under the same conditions, substituted boronic acids, boronates, and trialkylboranes were readily coupled with diaryl-, alkenyl-, and alkynyliodonium salts. Finally, the iodanes ArI(OH)OTs underwent cross-coupling with boronic acids, boronates, and trialkylboranes to afford biphenyls and aryl-substituted alkenes.