Fluoride-mediated dephosphonylation of alpha-diazo-beta-carbonyl phosphonates

TitleFluoride-mediated dephosphonylation of alpha-diazo-beta-carbonyl phosphonates
Publication TypeJournal Article
Year of Publication2017
AuthorsPhatake, RS, Mullapudi, V, Wakchaure, VC, Ramana, CV
JournalOrganic Letters
Volume19
Issue2
Pagination372-375
Date PublishedJAN
AbstractThe possibility of fluoride-mediated selective dephosphonylation of alpha-diazo-beta-carbonyl phosphonates such as the Ohira-Bestmann reagent has been proposed and executed. The resulting alpha-diazocarbonyl intermediates undergo a (3 + 2)pcycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess alpha-diazo-beta-carbonyl phosphonates) or Michael addition (with conjugated olefins).
DOI10.1021/acs.orglett.6b03573
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)6.732
Divison category: 
Organic Chemistry

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