A novel lanthanum metal-assisted reaction of diaryl ketones and electrophiles. Issue 8 (25th February 2015)

• Record Type: Journal Article
• Authors: Umeda, Rui; Ninomiya, Masashi; Nishino, Toshiaki; Kishida, Makoto; Toiya, Shunsuke; Saito, Tomoki; Nishiyama, Yutaka; Sonoda, Noboru
• Is Part Of: Tetrahedron. Volume 71:Issue 8(2015)
• Page Start: 1287
• Page End: 1291
• Publication Date: 2015-02-25
• Subjects: Lanthanum -- Diaryl ketone -- Electrophile; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2014.12.089
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A novel and efficient lanthanum metal-assisted carbon-carbon bond formation of diaryl ketones and various electrophiles, such as carbonyl compounds, esters, nitriles, and epoxides, has been developed. When diaryl ketones were allowed to react with dialkyl ketones in the presence of lanthanum metal and a catalytic amount of iodine, the cross pinacol coupling reaction proceeded to give the corresponding unsymmetrical 1, 2-diols in moderate to good yields. α-Hydroxy ketones were prepared by the lanthanum metal-assisted reaction of diaryl ketones with esters or nitriles, followed by hydrolysis with aq HCl. It is interesting to note that for the epoxides, the coupling reaction proceeded via the Meinwald rearrangement of epoxides to give the corresponding 1, 2-diols. Graphical abstract: