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Issue 8, 2018
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Overcoming solid handling issues in continuous flow substitution reactions through ionic liquid formation

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Abstract

Substitutions such as acylations, arylations, and alkylations are some of the most commonly run reactions for building complex molecules. However, the requirement of a stoichiometric base to scavange acid by-products creates significant challenges when operating in continuous flow due to solid handling issues associated with precipitating base·HX salts. We present a general and simple strategy to overcome these solid handling issues through the use of acid scavenging organic bases that generate low- to moderate-melting ionic liquids upon protonation. The application of these bases towards the most commonly run substitutions are demonstrated, enabling reactions to be run in flow without requiring additional equipment, specific solvents, or dilute reaction conditions to prevent clogging.

Graphical abstract: Overcoming solid handling issues in continuous flow substitution reactions through ionic liquid formation

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Publication details

The article was received on 24 Feb 2018, accepted on 22 Mar 2018 and first published on 29 Mar 2018


Article type: Communication
DOI: 10.1039/C8GC00618K
Citation: Green Chem., 2018,20, 1748-1753
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    Overcoming solid handling issues in continuous flow substitution reactions through ionic liquid formation

    S. K. Kashani, R. J. Sullivan, M. Andersen and S. G. Newman, Green Chem., 2018, 20, 1748
    DOI: 10.1039/C8GC00618K

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