Conversion of 1-alkenes into 1,4-diols through an auxiliary-mediated formal homoallylic C-H oxidation

Nugzar Ghavtadze, Ferdinand S. Melkonyan, Anton V. Gulevich, Chunhui Huang, Vladimir Gevorgyan

Research output: Contribution to journalArticle

71 Citations (Scopus)

Abstract

The ubiquitous nature of C-H bonds in organic molecules makes them attractive as a target for rapid complexity generation, but brings with it the problem of achieving selective reactions. In developing new methodologies for C-H functionalization, alkenes are an attractive starting material because of their abundance and low cost. Here we describe the conversion of 1-alkenes into 1,4-diols. The method involves the installation of a new Si,N-type chelating auxiliary group on the alkene followed by iridium-catalysed C-H silylation of an unactivated δ-C(sp 3)-H bond to produce a silolane intermediate. Oxidation of the C-Si bonds affords a 1,4-diol. The method is demonstrated to have broad scope and good functional group compatibility by application to the selective 1,4-oxygenation of several natural products and derivatives.

Original languageEnglish (US)
Pages (from-to)122-125
Number of pages4
JournalNature Chemistry
Volume6
Issue number2
DOIs
StatePublished - Feb 1 2014
Externally publishedYes

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Alkenes
Olefins
Oxidation
Iridium
Oxygenation
Chelation
Biological Products
Functional groups
Derivatives
Molecules
Costs

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Conversion of 1-alkenes into 1,4-diols through an auxiliary-mediated formal homoallylic C-H oxidation. / Ghavtadze, Nugzar; Melkonyan, Ferdinand S.; Gulevich, Anton V.; Huang, Chunhui; Gevorgyan, Vladimir.

In: Nature Chemistry, Vol. 6, No. 2, 01.02.2014, p. 122-125.

Research output: Contribution to journalArticle

Ghavtadze, Nugzar ; Melkonyan, Ferdinand S. ; Gulevich, Anton V. ; Huang, Chunhui ; Gevorgyan, Vladimir. / Conversion of 1-alkenes into 1,4-diols through an auxiliary-mediated formal homoallylic C-H oxidation. In: Nature Chemistry. 2014 ; Vol. 6, No. 2. pp. 122-125.
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