CHBr3/TiCl4/Mg as an Unusual Nucleophilic CBr2 Carbenoid: Effective and Chemoselective Dibromomethylenation of Aldehydes and Ketones

YR Bhorge, CT Chang, SH Chang…

Index: Bhorge, Yeshwant Ramchandra; Chang, Cheng-Ta; Chang, Su-Haur; Yan, Tu-Hsin European Journal of Organic Chemistry, 2012 , # 25 p. 4805 - 4810

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Abstract

Abstract We report that instead of using CBr 4, CHBr 3 can serve as a highly nucleophilic dibromomethylene carbenoid in chemoselective carbonyl dibromomethylenation. Successful application of the dibromomethylenation to various carbonyl compounds such as enolizable and sterically hindered ketones by using the CHBr 3/Mg/TiCl 4 system highlights the weakly basic nature, extraordinary reactivity, and synthetic versatility of the approach.