Jump to main content
Jump to site search

Issue 6, 2016
Previous Article Next Article

Low temperature dehydrations of non-activated alcohols via halide catalysis

Author affiliations

Abstract

Activating kinetically inert C–O bonds such as in primary alcohols is an important challenge for the transformation of biomass-derived feedstocks. The herein described methodology addresses this issue through a combination of halide and acid catalysis. The novel mechanistic pathway proposed based on detailed experimental studies enables selective olefin formation from alcohols – as opposed to ether formation – at relatively low temperatures. Suitable substrates are tertiary, secondary, and even primary alcohols. Furthermore, the observed selectivity for the Hoffman elimination product and the realization of a non-rearranging Friedel–Crafts alkylation suggest that the reaction medium with high concentrations of halide (NBu4Br) enables reaction outcomes that cannot be obtained through carbocation intermediates.

Graphical abstract: Low temperature dehydrations of non-activated alcohols via halide catalysis

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Feb 2016, accepted on 06 Apr 2016 and first published on 07 Apr 2016


Article type: Research Article
DOI: 10.1039/C6QO00069J
Citation: Org. Chem. Front., 2016,3, 701-708
  •   Request permissions

    Low temperature dehydrations of non-activated alcohols via halide catalysis

    X. Zhang, S. J. Desrochers, A. D. Carl, N. Geagea, K. Zielinski and M. H. Emmert, Org. Chem. Front., 2016, 3, 701
    DOI: 10.1039/C6QO00069J

Search articles by author

Spotlight

Advertisements