N-Heterocyclic Carbene Catalyzed Intramolecular Hydroacylation of Alkynylphosphonates

Zhenqiang Wang; Zhihua Yu; Ying Wang; Deqing Shi

doi:10.1055/s-0031-1290976

Synthesis, Table of Contents

Synthesis 2012; 44(10): 1559-1568
DOI: 10.1055/s-0031-1290976

paper

N-Heterocyclic Carbene Catalyzed Intramolecular Hydroacylation of Alkynylphosphonates

Zhenqiang Wang

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041 Email: chshidq@mail.ccnu.edu.cn

,

Zhihua Yu

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041 Email: chshidq@mail.ccnu.edu.cn

,

Ying Wang

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041 Email: chshidq@mail.ccnu.edu.cn

,

Deqing Shi*

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041 Email: chshidq@mail.ccnu.edu.cn

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Abstract

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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.

Key words

Stetter reaction - N-heterocyclic carbenes - hydroacylation - one-pot synthesis - chromone - phosphonate

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References

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