A general, stereospecific, and straightforward method for the rapid preparation of functionalized (E)-monofluoroenamines is reported. Rather than transition metals (Rh, Ni, Pd, Cu, Ag, etc.), Et2O·BF3 was employed to promote… Click to show full abstract
A general, stereospecific, and straightforward method for the rapid preparation of functionalized (E)-monofluoroenamines is reported. Rather than transition metals (Rh, Ni, Pd, Cu, Ag, etc.), Et2O·BF3 was employed to promote the formation of α-diazoimine through the Dimroth equilibrium of common 1-sulfonyl-1,2,3-triazole for the first time. An overall migration of fluoride from boron to the diazo-linked carbon of α-diazoimine was achieved. Derivations and late-stage modification of bioactive molecule were conducted. A plausible mechanism was also proposed.
Journal Title: Organic letters
Year Published: 2018
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