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Reduction of esters to ethers

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TiCl4 mediates a facile and selective room temperature deoxygenation of both aromatic and aliphatic carboxylic esters to ethers in the presernce of BH3-NH3. This process is compatible with various potentially sensitive functional groups. Substituting TiCl4 by BF3-Et2O  alters the reaction pathway, reducing esters to alcohols.
P. V. Ramachandran, A. A. Alawaed, H. J. Hamann, Org. Lett., 2023, 25, 6902-6906.


A novel one-pot procedure for a directly reductive conversion of esters to the corresponding ethers by Et3SiH in the presence of a catalytic amount of InBr3 is described. This simple catalytic system appeared to be remarkably tolerant to several functional groups.
N. Sakai, T. Moriya, T. Konakahara, J. Org. Chem., 2007, 72, 5920-5922.