Kang Suk-Ku, Lee Hong-Woo, Jang Su-Bum, Ho Pil-Su
Department of Chemistry, Sung Kyun Kwan University, Natural Science Campus, Suwon 440-746, Korea.
J Org Chem. 1996 Jul 12;61(14):4720-4724. doi: 10.1021/jo960195m.
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.
在无碱的水性条件下，于室温实现了碘鎓盐（碘鎓盐和碘烷）与有机硼化合物的钯催化交叉偶联反应以形成碳 - 碳键。在水性条件下，在Pd(PPh(3))(4)（0.2 mol%）或Pd(OAc)(2)（0.2 mol%）存在下，苯基硼酸与四氟硼酸二苯基碘鎓盐偶联，几乎以定量产率得到联苯。在相同条件下，取代硼酸、硼酸酯和三烷基硼烷很容易与二芳基、烯基和炔基碘鎓盐偶联。最后，碘烷ArI(OH)OTs与硼酸、硼酸酯和三烷基硼烷进行交叉偶联，得到联苯和芳基取代的烯烃。
