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Photochemical Doyle-Kirmse.pdf (614.78 kB)
Photochemical Doyle-Kirmse Reaction – a Metal-Free Route to Allenes
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 12.11.2019, 16:35 and posted on 25.11.2019, 11:52by 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.