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reductive dehalogenation of halo ketones
Reductive dehalogenations of halo ketones are organic reactions that result in the formation of ketones and functionalized derivatives of ketones from α-halo ketones in the presence of metallic reducing agents.〔Noyori, R.; Hayakawa, Y. ''Org. React.'' 1983, ''29'', 163. 〕
==Introduction==
α-Halo ketones are readily prepared from enolates by treatment with electrophilic halogen sources.〔Oestreich, M ''Angew. Chem. Int. Ed.'' 2005, ''44'', 2324.〕 The reduction of α-halo ketones generates reactive intermediates that may exhibit unique substitution patterns and reactivity. For instance, reduction of α,α'-dihalo ketones leads to 2-oxyallyl metal complexes, which participate in () and () cycloaddition reactions as the 2π component.〔Rigby, J.; Pigge, C. ''Org. React.'' 1997, ''51'', 351.〕 2-Oxyallyl metal intermediates may also intercept nucleophiles in a process that involves umpolung at the α carbon.〔Fry, J. ; O'Dea, J. ''J. Org. Chem.'' 1975, ''40'', 3625.〕 In addition, because reduction of monohalo ketones produces enolates in a site-specific fashion, reactions associated with enolates (alkylation, aldol, Michael) may be carried out using halo ketone substrates under reductive conditions.
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