CHBr 3 /TiCl 4 /Mg as an Unusual Nucleophilic CBr 2 Carbenoid: Effective and Chemoselective Dibromomethylenation of Aldehydes and Ketones

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 t...

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Bibliographic Details
Published in:European journal of organic chemistry 2012-09, Vol.2012 (25), p.4805-4810
Main Authors: Bhorge, Yeshwant Ramchandra, Chang, Cheng‐Ta, Chang, Su‐Haur, Yan, Tu‐Hsin
Format: Article
Language:English
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Summary: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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200457