ol6b03573_si_003.cif (12.23 kB)

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

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posted on 30.12.2016, 15:49 by Ravindra S. Phatake, Venkannababu Mullapudi, Vivek C. Wakchaure, Chepuri V. Ramana
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 N-acylation (with excess α-diazo-β-carbonyl phosphonates) or Michael addition (with conjugated olefins).