Reaction of Highly Volatile Organic Compounds with Organolithium Species in Flow Microreactor

Abstract

Highly volatile organic compounds (VOCs) with boiling point (bp) around/below room temperature are generally difficult to manipulate precisely in liquid-phase organic reaction despite their significant atom-economic advantages. We have developed a novel approach using a jacketed syringe pump to enable the formylation of organolithium species in a continuous flow system under the ambient pressure. Methyl formate (bp 32 °C) worked as a formylating agent and was successfully delivered to the continuous operation for over 30 minutes in our microflow system. This methodology was successfully expanded to the application to acetaldehyde (bp 21 °C) and heptafluoropropyl bromide (bp 12 °C).