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Photochemical Doyle-Kirmse Reaction – a Metal-Free Route to Allenes
preprintsubmitted on 12.11.2019, 16:35 and posted on 25.11.2019, 11:52 by katarzyna Orłowska, Katarzyna Rybicka-Jasińska, Piotr Krajewski, Dorota Gryko
This report describes metal-free, blue light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yields. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.