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Synthesis 2012; 44(10): 1559-1568
DOI: 10.1055/s-0031-1290976
DOI: 10.1055/s-0031-1290976
paper
N-Heterocyclic Carbene Catalyzed Intramolecular Hydroacylation of Alkynylphosphonates
Further Information
Publication History
Received: 13 January 2012
Accepted after revision: 24 March 2012
Publication Date:
02 May 2012 (online)
Abstract
Two exocyclic and endocyclic olefin tautomers of chromone phosphonates were obtained in good to excellent yields at different temperatures by utilizing an N-heterocyclic carbene catalyst in the intramolecular reactions between the formyl group and alkynylphosphonates. The exocyclic olefins can isomerize to the endocyclic derivatives completely when treated with a thiazolium salt precatalyst and potassium carbonate at 30 °C for three to five hours. In addition, the chromone phosphonate derivatives were also applied in the one-pot synthesis of benzopyranopyridine phosphonates in moderated yields.
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For reviews, see:
For recent reviews on NHC catalysis, see:
For synthetic routes to the NHC precursors, see: