Experimental and computational study demonstrates transition-metal-free cross-coupling of enaminones, highlighting boron-directed oxygen coordination for remote bond formation.
We report a transition-metal-free cross-coupling reaction of potassium organotrifluoroborates and enaminones, enabled by PhBF2-mediated O-coordinated 1,5-migration in tetracoordinate boron intermediates. This activates weakly coordinating carbonyl oxygen for efficient functionalization and offers new insights into organoboron-mediated carbonyl activation. Mechanistic and DFT studies confirm the O-coordinated pathway is kinetically favored over N-coordinated 1,3-migration, with the native amino group as a traceless leaving group for remote C–C bond formation.
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Zhang et al. (2026) studied this question.
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