Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using Smi2 and D2O as deuterium source under set conditions

Michal Szostak, Malcolm Spain, David J. Procter

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The first general method for the chemoselective synthesis of α,α-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.

Original languageEnglish (US)
Pages (from-to)5052-5055
Number of pages4
JournalOrganic letters
Volume16
Issue number19
DOIs
StatePublished - Oct 3 2014

Fingerprint

Lewis Bases
Alkali Metals
deuterides
Lewis base
Deuterium
Carboxylic Acids
carboxylic acids
alkali metals
Feedstocks
deuterium
electron transfer
alcohols
Chemical activation
Alcohols
activation
Electrons
Substrates
synthesis

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using Smi2 and D2O as deuterium source under set conditions. / Szostak, Michal; Spain, Malcolm; Procter, David J.

In: Organic letters, Vol. 16, No. 19, 03.10.2014, p. 5052-5055.

Research output: Contribution to journalArticle

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