Fluoride-Mediated Dephosphonylation of α‑Diazo-β-carbonyl Phosphonates

The possibility of fluoride-mediated selective dephosphonylation of α-diazo-β-carbonyl phosphonates such as the Ohira–Bestmann reagent has been proposed and executed. The resulting α-diazocarbonyl intermediates undergo a (3 + 2)-cycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either <i>N</i>-acylation (with excess α-diazo-β-carbonyl phosphonates) or Michael addition (with conjugated olefins)

Fluoride-Mediated Dephosphonylation of α‑Diazo-β-carbonyl Phosphonates

The possibility of fluoride-mediated selective dephosphonylation of α-diazo-β-carbonyl phosphonates such as the Ohira–Bestmann reagent has been proposed and executed. The resulting α-diazocarbonyl intermediates undergo a (3 + 2)-cycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either <i>N</i>-acylation (with excess α-diazo-β-carbonyl phosphonates) or Michael addition (with conjugated olefins)