Cyclic Diaryl λ<sup>3</sup>-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions
Matteo Lanzi, Racha Abed Ali Abdine, Maxime De Abreu, Joanna Wencel‐Delord
Abstract
Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.
Topics & Concepts
Pericyclic reactionChemistryCycloadditionAtom economyCombinatorial chemistryAtom (system on chip)Reaction conditionsOrganic synthesisFunctional groupComputational chemistryCatalysisOrganic chemistryComputer scienceParallel computingPolymerOxidative Organic Chemistry ReactionsChemical synthesis and alkaloidsSynthetic Organic Chemistry Methods