We have synthesized a new nickel enolate [(PhCOCF2)Ni(dcpe)][FB(C6F5)3] featuring fluorine atoms on the enolate moiety via B(C6F5)3-promoted C-F bond activation of α,α,α-trifluoroacetophenone. X-ray diffraction study of [(PhCOCF2)Ni(dcpe)][FB(C6F5)3] revealed that the complex had adopted an η(3)-oxallyl coordination mode in the crystal lattice. The reaction of (t)BuNC with [(PhCOCF2)Ni(dcpe)][FB(C6F5)3] resulted in the coordination of isocyanide to the nickel center to form a C-bound enolate complex. The reactions of [(PhCOCF2)Ni(dcpe)][FB(C6F5)3] with aldehydes gave insertion products quantitatively which were fully characterized by NMR spectroscopy. Furthermore, we established unique catalytic applications for [(PhCOCF2)Ni(dcpe)][FB(C6F5)3] toward a Tishchenko reaction, along with a highly selective crossed-esterification of α,α,α-trifluoroacetophenones with aldehydes.
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