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

doi:10.1021/ol502404e

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

Rutgers Newark, Chemistry

Research output: Contribution to journal › Article

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 language	English (US)
Pages (from-to)	5052-5055
Number of pages	4
Journal	Organic letters
Volume	16
Issue number	19
DOIs	https://doi.org/10.1021/ol502404e
State	Published - 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

Szostak, M., Spain, M., & Procter, D. J. (2014). Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using Smi₂ and D₂O as deuterium source under set conditions. Organic letters, 16(19), 5052-5055. https://doi.org/10.1021/ol502404e

Szostak, Michal ; Spain, Malcolm ; Procter, David J. / Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using Smi₂ and D₂O as deuterium source under set conditions. In: Organic letters. 2014 ; Vol. 16, No. 19. pp. 5052-5055.

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Szostak, M, Spain, M & Procter, DJ 2014, 'Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using Smi₂ and D₂O as deuterium source under set conditions', Organic letters, vol. 16, no. 19, pp. 5052-5055. https://doi.org/10.1021/ol502404e

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 journal › Article

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Szostak M, Spain M, Procter DJ. Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using Smi₂ and D₂O as deuterium source under set conditions. Organic letters. 2014 Oct 3;16(19):5052-5055. https://doi.org/10.1021/ol502404e

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10.1021/ol502404e