Bromoform Activation. TiCl4–Mg-Promoted CHBr2 – and CBr3 – Transfer to a Variety of Aldehydes and Ketones

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...

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Bibliographic Details
Published in:Organic letters 2013-11, Vol.15 (22), p.5802-5805
Main Authors: Yan, Tu-Hsin, Chang, Su-Haur, Chang, Cheng-Ta, Lin, Chia-Kuan, Liu, Chien-Yu
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402861a