Investigations of the generality of quaternary ammonium salts as alkylating agents in direct C–H alkylation reactions: solid alternatives for gaseous olefins

Literature Information

Publication Date 2019-03-28
DOI 10.1039/C9OB00243J
Impact Factor 3.876
Authors

David Schönbauer, Manuel Spettel, Ernst Pittenauer, Michael Schnürch


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Abstract

C–H alkylation reactions using short chain olefins as alkylating agents could be operationally simplified on the lab scale by using quaternary ammonium salts as precursors for these gaseous reagents: Hofmann elimination delivers in situ the desired alkenes with the advantage that the alkene concentration in the liquid phase is high. In case a catalytic system did not tolerate the conditions for Hofmann elimination, a very simple spatial separation of both reactions, Hofmann elimination and direct alkylation, was achieved to circumvent possible side reactions or catalyst deactivation. Additionally, the truly catalytically active species of a rhodium(I) mediated alkylation reaction could be identified by using this approach.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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