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Rh(I)-Catalyzed CO Gas-Free Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Using Formaldehyde

Tsumoru Morimoto*, Kae Yamasaki, Akihisa Hirano, Ken Tsutsumi, Natsuko Kagawa, Kiyomi Kakiuchi, Yasuyuki Harada, Yoshiya Fukumoto, Naoto Chatani and Takanori Nishioka

*Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0192, Japan, Email: morimotoms.naist.jp

T. Morimoto, K. Yamasaki, A. Hirano, K. Tsutusmi, N. Kagawa, K. Kakiuchi, Y. Harada, Y. Fukukomoto, N. Chatani, T. Nishioka, Org. Lett., 2009, 11, 1777-1780.

DOI: 10.1021/ol900327x


Abstract

In the presence of a rhodium catalyst, paraformaldehyde enables a CO gas-free carbonylative cyclization of alkynes with 2-bromophenylboronic acids to yield indenone derivatives. Rhodium-catalyzed decarbonylation of formaldehyde is followed by carbonylation of alkynes with 2-haloboronic acids, respectively, leading to efficient whole carbonylation.

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Key Words

Indenones, Multicomponent Reactions


ID: J54-Y2009-1320