4.8 Article

Selective Synthesis of α,α-Dideuterio Alcohols by the Reduction of Carboxylic Acids Using SmI2 and D2O as Deuterium Source under SET Conditions

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ORGANIC LETTERS
卷 16, 期 19, 页码 5052-5055

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AMER CHEMICAL SOC
DOI: 10.1021/ol502404e

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  1. EPSRC
  2. Leverhulme Trust
  3. EPSRC [EP/I004017/1] Funding Source: UKRI
  4. Engineering and Physical Sciences Research Council [EP/I004017/1] Funding Source: researchfish

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The first general method for the chemoselective synthesis of alpha,alpha-dideuterio alcohols directly from feedstock carboxylic acids under single electron transfer conditions using SmI2 is reported. This reaction proceeds after the activation of Sm(II) with a Lewis base, results in excellent levels of deuterium incorporation across a wide range of substrates, and represents an attractive alternative to processes mediated by pyrophoric alkali metal deuterides.

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