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....

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Bibliographic Details
Published in:Organic letters 2017-01, Vol.19 (2), p.372-375
Main Authors: Phatake, Ravindra S, Mullapudi, Venkannababu, Wakchaure, Vivek C, Ramana, Chepuri V
Format: Article
Language:English
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Summary: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).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03573