Fluoride-mediated dephosphonylation of α-diazo-β-carbonyl phosphonates

Phatake, Ravindra S. ; Mullapudi, Venkannababu ; Wakchaure, Vivek C. ; Ramana, Chepuri V. (2017) Fluoride-mediated dephosphonylation of α-diazo-β-carbonyl phosphonates Organic Letters, 19 (2). pp. 372-375. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b...

Related URL: http://dx.doi.org/10.1021/acs.orglett.6b03573


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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ID Code:105871
Deposited On:01 Feb 2018 16:49
Last Modified:01 Feb 2018 16:49

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