Modular Synthesis of Stereodefined Benzocyclobutene Derivatives via Sequential Cu- and Pd-Catalysis
Fabien J. T. Talbot, Shibo Zhang, Bishnupada Satpathi, Gareth P. Howell, Gregory J. P. Perry, Giacomo E. M. Crisenza, David J. Procter
Abstract
Benzocyclobutenes (BCBs) are of growing interest in materials and medicinal chemistry, although general routes for their provision remain underexplored. A modular, divergent, and stereoselective Cu- and Pd-catalyzed assembly/cyclization sequence allows the synthesis of densely functionalized BCBs, from readily accessible imine, allene, and diboron precursors. Preliminary results have identified enantioselective conditions for our protocol and highlighted, for example, its applicability to the synthesis of BCB-containing peptides. By simple variation of experimental conditions or substrate modification, our strategy was expanded to deliver indoline and quinoline derivatives, suitable for further manipulations.