Fluoride-Mediated Dephosphonylation of α-Diazo-β-carbonyl Phosphonates
Ravindra S Phatake1, Venkannababu Mullapudi1, Vivek C Wakchaure1
1Organic Chemistry Division, CSIR-National Chemical Laboratory , Dr. HomiBhabha Road, Pune 411008, India.
Abstract:
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).
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