Chemical synthesis study demonstrates selective reduction of esters to ethers or alcohols using borane–ammonia, highlighting catalyst-controlled reaction divergence at room temperature.
A facile and selective room temperature deoxygenation of both aromatic and aliphatic carboxylic esters to ethers has been achieved by regulating the stoichiometry of the reductant, BH 3 –NH 3, and the catalyst, TiCl 4 . This first, practical borane-mediated process is compatible with various potentially sensitive functional groups and is applicable to the deoxygenative ether formation from typically challenging aromatic acid esters. Substituting BF 3 –Et 2 O as the catalyst alters the reaction pathway, reducing the esters to alcohols. Mechanistic insights are provided by NMR spectroscopy, deuterium labeling, and kinetic isotope studies.
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Ramachandran et al. (2023) studied this question.
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