Substituent controlled reactivity switch: selective synthesis of α-diazoalkylphosphonates or vinylphosphonates via nucleophilic substitution of alkyl bromides with Bestmann-Ohira reagent

We report a substituent controlled nucleophilic displacement of alkyl bromides with Bestmann-Ohira reagent yielding either dimethyl diazoalkylphosphonates or (E)-vinylphosphonates. The dimethyl diazoalkylphosphonates could be readily converted into corresponding (E)-vinylphosphonates in the presence...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-11, Vol.50 (85), p.12896-12898
Main Authors: Pramanik, Mukund M D, Chaturvedi, Atul Kumar, Rastogi, Namrata
Format: Article
Language:English
Subjects:
Alkylation
Azo Compounds - chemical synthesis
Azo Compounds - chemistry
Bromides
Bromides - chemistry
Copper - chemistry
Cyclization
Dimethyl
Displacement
Indicators and Reagents
Nitrogen
Organophosphonates - chemical synthesis
Organophosphonates - chemistry
Pyrazoles - chemical synthesis
Reagents
Switches
Synthesis
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Summary:We report a substituent controlled nucleophilic displacement of alkyl bromides with Bestmann-Ohira reagent yielding either dimethyl diazoalkylphosphonates or (E)-vinylphosphonates. The dimethyl diazoalkylphosphonates could be readily converted into corresponding (E)-vinylphosphonates in the presence of Cu following nitrogen elimination in quantitative yields.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc05684a