Low temperature dehydrations of non-activated alcohols via halide catalysis
Literature Information
Publication Date
2016-04-07
DOI
10.1039/C6QO00069J
Impact Factor
5.281
Authors
X. Zhang, S. J. Desrochers, A. D. Carl, N. Geagea, K. Zielinski, M. H. Emmert
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
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CAS Number:
1279090-25-3
Molecular Formula:
C20H30BNO5
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[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid
CAS Number:
50918-26-8
Molecular Formula:
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