Ruthenium-catalyzed functionalization of aryl carbon-oxygen bonds in aromatic ethers with organoboron compounds

Fumitoshi Kakiuchi; Mayumi Usui; Satoshi Ueno; Naoto Chatani; Shinji Murai

doi:10.1021/ja0393170

Ruthenium-catalyzed functionalization of aryl carbon-oxygen bonds in aromatic ethers with organoboron compounds

J Am Chem Soc. 2004 Mar 10;126(9):2706-7. doi: 10.1021/ja0393170.

Authors

Fumitoshi Kakiuchi¹, Mayumi Usui, Satoshi Ueno, Naoto Chatani, Shinji Murai

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. kakiuchhi@chem.edg.osaka-u.ac.jp

PMID: 14995180
DOI: 10.1021/ja0393170

Abstract

The ruthenium-catalyzed reaction of aryl ethers having a carbonyl group at the ortho position to the ether group with organoboronates (R-B(OCH2CMe2CH2O), R = aryl, alkenyl, and alkyl) resulted in site-selective C-C bond formation. Among the transition metal complexes screened, the RuH2(CO)(PPh3)3 complex showed the highest activity. Several aromatic ketones having methoxy or phenoxy groups at the ortho position can also be used in this coupling reaction. A variety of arylboronates containing electron-donating (NMe2, OMe, methyl, and vinyl) and -withdrawing (F and CF3) groups reacted with methoxy ketones to give the corresponding coupling products in high yields.