Palladium-catalyzed cross-coupling reaction of organoindiums with aryl halides in aqueous media

K Takami; H Yorimitsu; H Shinokubo; S Matsubara; K Oshima

doi:10.1021/ol015975i

Palladium-catalyzed cross-coupling reaction of organoindiums with aryl halides in aqueous media

Org Lett. 2001 Jun 28;3(13):1997-9. doi: 10.1021/ol015975i.

Authors

K Takami¹, H Yorimitsu, H Shinokubo, S Matsubara, K Oshima

Affiliation

¹ Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 11418033
DOI: 10.1021/ol015975i

Abstract

[reaction: see text] Diaryl-, divinyl-, and dialkylindium proved to be stable in aqueous media and to undergo a palladium-catalyzed cross-coupling reaction with aryl halides in aqueous THF. Treatment of 3-iodophenol with diphenylindium compound, generated from indium trichloride and two equimolar amounts of a phenyl Grignard reagent, in aqueous media under palladium catalysis provided the corresponding coupling product in excellent yield. Divinyl- and diethylindium can be used for the coupling reaction in the presence of water. A wide range of functional groups, including a hydroxy group and a formyl group, are compatible with this reaction.