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; Takanori Nishioka

doi:10.1021/ol900327x

Rh(I)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde

Org Lett. 2009 Apr 16;11(8):1777-80. doi: 10.1021/ol900327x.

Authors

Tsumoru Morimoto¹, Kae Yamasaki, Akihisa Hirano, Ken Tsutsumi, Natsuko Kagawa, Kiyomi Kakiuchi, Yasuyuki Harada, Yoshiya Fukumoto, Naoto Chatani, Takanori Nishioka

Affiliation

¹ Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0192, Japan.

PMID: 19301863
DOI: 10.1021/ol900327x

Abstract

The rhodium(I)-catalyzed reaction of alkynes with 2-bromophenylboronic acids in the presence of paraformaldehyde resulted in a CO gas-free carbonylative cyclization, yielding indenone derivatives. [RhCl(BINAP)](2) and [RhCl(cod)](2) were responsible for the decarbonylation of formaldehyde and the subsequent carbonylation of alkynes with 2-haloboronic acids, respectively, leading to efficient whole carbonylation. Sterically bulky and electron-withdrawing groups on unsymmetrically substituted alkynes favored the alpha-position of indenones.