One-pot, oxidative and selective conversion of benzylic silyl and tetrahydropyranyl ethers to gem-dichlorides using trichloroisocyanuric acid and triphenylphosphine as an efficient and neutral system

Abstract

A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh₃) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides in good to excellent yields. The present method shows a high degree of chemoselectivity, and due to its one-pot nature is in accordance with green chemistry.

Graphical Abstract

Keywords:

• Trimethylsilyl ether
• tetrahydropyranyl ether
• gem-dichloride
• trichloroisocyanuric acid
• triphenylphosphine

Acknowledgements

The authors gratefully acknowledge the support of this work by the Damghan University Research Council.