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Synfacts 2010(8): 0941-0941  
DOI: 10.1055/s-0030-1257752
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Difluoromethylation of Lithium Enolates with Trifluoromethyl Iodide

Contributor(s): Paul Knochel, Tobias Thaler
K. Mikami*, Y. Tomita, Y. Itoh
Tokyo Institute of Technology and The University of Tokyo, Japan
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Publikationsdatum:
22. Juli 2010 (online)

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Significance

α-Difluoromethylation of lithium enolates was efficiently effected with trifluoro­methyl iodide. Remarkably, the reaction proceeds via preferential cleavage of a C-F bond over the weaker C-I bond. This unprecedented reaction enables the straightforward construction of difluoromethyl-attached all-carbon quaternary centers. The remaining iodide functionality allows further functionalization.