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Publication - Dr Adam Noble

    Photoredox-Catalyzed Cyclobutane Synthesis via a Deboronative Radical Addition-Polar Cyclization Cascade

    Citation

    Shu, C, Noble, A & Aggarwal, VK, 2019, ‘Photoredox-Catalyzed Cyclobutane Synthesis via a Deboronative Radical Addition-Polar Cyclization Cascade’. Angewandte Chemie - International Edition, vol 58., pp. 3870-3874

    Abstract

    Photoredox-catalyzed methylcyclobutanations of alkylboronic esters are described. The reactions proceed through single-electron transfer induced deboronative radical addition to an electron-deficient alkene followed by single-electron reduction and polar 4-exo-tet cyclization with a pendant alkyl halide. Key to the success of the methodology was the use of easily oxidizable arylboronate complexes. Structurally diverse cyclobutanes are shown to be conveniently prepared from readily available alkylboronic esters and a range of haloalkyl alkenes. The mild reactions display excellent functional group tolerance, and the radical addition-polar cyclization cascade also enables the synthesis of 3-, 5-, 6-, and 7-membered rings.

    Full details in the University publications repository