Abstract

New Continuous Flow Synthetic Methods with Highly Reactive Intermediates

Hélène Lebel, Professor, Department of Chemistry, University of Montreal

Continuous flow technology offers many advantages, including the safe manipulation of highly reactive intermediates.  As such, a number of methods for the preparation and the use of diazo reagents in continuous flow have been described in the literature. Another class of highly reaction intermediates that benefit from continuous flow technology are aliphatic diazonium intermediates. The Lebel group has shown that aliphatic diazoniums can be in-situ generated from an amine and a nitrite reagent in the presence of an acid. The reaction conditions are compatible with a large variety of functional groups. The trapping of aliphatic diazoniums with carboxylates, electron rich aromatics and other nucleophiles afforded various synthetic compounds in high yields.  The optimization details and the scope of this methods will be described in this presentation.