Low temperature dehydrations of non-activated alcohols via halide catalysis

文献情報

出版日 2016-04-07

DOI 10.1039/C6QO00069J

インパクトファクター 5.281

著者

X. Zhang, S. J. Desrochers, A. D. Carl, N. Geagea, K. Zielinski, M. H. Emmert

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Low temperature dehydrations of non-activated alcohols via halide catalysis

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