General Ether Synthesis under Mild Acid-Free Conditions. Trimethylsilyl Iodide Catalyzed Reductive Coupling of Carbonyl Compounds with Trialkylsilanes to Symmetrical Ethers and Reductive Condensation with Alkoxysilanes to Unsymmetrical Ethers

Article abstract of DOI:10.1021/jo00228a031

Facile synthesis of symmetrical ethers is achieved by either trimethylsilyl triflate or trimethylsilyl iodide catalyzed reductive coupling of carbonyl compounds (aldehydes and ketones) with trialkylsilanes.The method was also extended to the trimethylsilyl iodide catalyzed preparation of unsymmetrical ethers by reductive condensation (of carbonyl compounds) with alkoxysilanes.The scope and limitations of the reactions are discussed with emphasis on diastereoselectivity.