Silica Chloride-Catalyzed One-Pot Isomerization–Chlorination, Arylation, and Etherification of Baylis–Hillman Adducts

Ponnusamy Shanmugam; Baby Viswambharan; Vadivel Vaithiyanathan

doi:10.1071/CH07123

RESEARCH ARTICLE

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Silica Chloride-Catalyzed One-Pot Isomerization–Chlorination, Arylation, and Etherification of Baylis–Hillman Adducts

Ponnusamy Shanmugam ^A ^B , Baby Viswambharan ^A and Vadivel Vaithiyanathan ^A

+ Author Affiliations

- Author Affiliations

^A Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-695 019, Kerala, India.

^B Corresponding author. Email: shanmu196@rediffmail.com

Australian Journal of Chemistry 60(11) 850-856 https://doi.org/10.1071/CH07123
Submitted: 25 April 2007 Accepted: 1 August 2007 Published: 1 November 2007

Abstract

A convenient and efficient one-pot isomerization–chlorination, arylation, and etherification of several Baylis–Hillman adducts with silica chloride, an eco-friendly heterogeneous catalyst, silica chloride–arenes, and silica chloride–saturated and unsaturated alcohols as reagent systems are reported. These reactions furnished highly functionalized isomerized Baylis–Hillman derivatives in good yield. The efficiency and necessity of silica chloride catalyst was compared with thionyl chloride. A plausible mechanism of the reaction is proposed.

Acknowledgements

P.S. thanks Professor Dr T.K. Chandrashekar, Director-NIST, for infrastructure facilities. Financial support (SR/S1/OC-38/2005) from the DST (New Delhi) is gratefully acknowledged. B.V. and V.V. thank CSIR (New Delhi) for the award of a Senior Research Fellowship. Constructive suggestions for the improvement of the manuscript from the referees are greatly acknowledged.

References

Silica Chloride-Catalyzed One-Pot Isomerization–Chlorination, Arylation, and Etherification of Baylis–Hillman Adducts

Abstract

Acknowledgements

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