Iridium-catalyzed hydroboration of alkenes with pinacolborane

Yasunori Yamamoto, Rhyou Fujikawa, Tomokazu Umemoto and Norio Miyaura*

*Division of Molecular Chemistry, Faculty of Engineering, Hokkaido University, Sapporo 060-8628, Japan, Email: miyauraorg-mc.eng.hokudai.ac.jp

Y. Yamamoto, R. Fujikawa, T. Umemoto, N. Miyaura, Tetrahedron, 2004, 60, 10695-10700.

DOI: 10.1016/j.tet.2004.09.014

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Abstract

Hydroboration of terminal and internal aliphatic alkenes with pinacolborane was carried out at room temperature in the presence of dppm and [Ir(cod)Cl]₂ resulting in addition of the boron atom to the terminal carbon with a selectivity of more than 99%. A complex prepared from dppe and [Ir(cod)Cl]₂ resulted in the best yields for vinylarenes.

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Key Words

Hydroboration, Alkylboronates, Pinacolborane, Iridium, Rhodium

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ID: J72-Y2004-1010