Investigations of the generality of quaternary ammonium salts as alkylating agents in direct C–H alkylation reactions: solid alternatives for gaseous olefins. Issue 16 (5th April 2019)

• Record Type: Journal Article
• Authors: Schönbauer, David; Spettel, Manuel; Pollice, Robert; Pittenauer, Ernst; Schnürch, Michael
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 16(2019)
• Page Start: 4024
• Page End: 4030
• Publication Date: 2019-04-05
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00243j
• Languages: English
• ISSNs: 1477-0520

Abstract

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. 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.