Expedient Diels-Alder cycloadditions with ortho-quinodimethanes in a high temperature/pressure flow reactorElectronic supplementary information (ESI) available: Optimization study details, experimental procedures, characterization data, copies of 1H, 13C and 2D NMR spectra. See DOI: 10.1039/c7re00058h

We describe herein Diels-Alder cycloadditions enabled by the efficient ring-opening of benzocyclobutenes and benzothiophene-2,2-dioxides using a high temperature/pressure flow reactor. The resultant ortho -quinodimethanes were generated and subsequently reacted with a wide range of dienophiles to provide complex heterocyclic ring systems. The use of flow technology allowed these reactions to be completed within minutes using conventional, readily removed solvents. We describe herein Diels-Alder cycloadditions enabled by the efficient ring-opening of benzocyclobutenes and benzothiophene-2,2-dioxides using a high temperature/pressure flow reactor.