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Bromoform Activati . TiCl4Mg-Promoted CHBr2and CBr3Transferto a Variety of Aldehydes and Ketones

By Tu-Hsin Yan, Su-Haur Chang, Cheng-Ta Chang, Chia-Kuan Lin and Chien-Yu Liu


TiCl4–Mg can mediate addition of CHBr3 to a variety of aldehydes and ketones to form dibromomethyl carbinols and also be used to effect CBr3 transfer to carbonyl groups to form tribromomethyl carbinols. The successful application of TiCl4–Mg-promoted coupling of CHBr3 with various carbonyl compounds, especially in the case of highly enolizable ketones such as 2-indanone and β-tetralone, highlights the extraordinary reactivity and selectivity and the weakly basic nature of this system

Year: 2014
DOI identifier: 10.1021/ol402861a
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