Development of a Selective Friedel–Crafts Alkylation Surrogate: Safe Operating Conditions through Mechanistic Understanding

This article describes a selective one-pot, Friedel–Crafts acylation/ketone reduction protocol, effectively a surrogate for the Friedel–Crafts alkylation reaction with a primary alkyl halide. A potentially dangerous failure mode was identified, resulting in the uncontrolled evolution of hydrogen. A...

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Bibliographic Details
Published inOrganic process research & development Vol. 16; no. 12; pp. 2043 - 2050
Main Authors Bream, Robert N, Hulcoop, David G, Gooding, Steve J, Watson, Simon A, Blore, Charlotte
Format Journal Article
LanguageEnglish
Published American Chemical Society 21.12.2012
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Summary:This article describes a selective one-pot, Friedel–Crafts acylation/ketone reduction protocol, effectively a surrogate for the Friedel–Crafts alkylation reaction with a primary alkyl halide. A potentially dangerous failure mode was identified, resulting in the uncontrolled evolution of hydrogen. A series of mechanistic experiments, including analysis by 27Al NMR, was undertaken, and the reaction mechanism elucidated. Finally, the use of React IR to ensure real-time reaction safety was demonstrated.
ISSN:1083-6160
1520-586X
DOI:10.1021/op300257z