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CHBr 3 /TiCl 4 /Mg as an Unusual Nucleophilic CBr 2 Carbenoid: Effective and Chemoselective Dibromomethylenation of Aldehydes and Ketones
Author(s) -
Bhorge Yeshwant Ramchandra,
Chang ChengTa,
Chang SuHaur,
Yan TuHsin
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200457
Subject(s) - carbenoid , chemistry , nucleophile , reactivity (psychology) , steric effects , nucleophilic addition , medicinal chemistry , organic chemistry , combinatorial chemistry , computational chemistry , catalysis , rhodium , medicine , alternative medicine , pathology
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.