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Photochemical Doyle-Kirmse Reaction – a Metal-Free Route to Allenes

preprint
submitted on 12.11.2019 and posted on 25.11.2019 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.

Funding

Foundation for Polish Science, TEAM POIR.04.04.00-00-4232/17-00, Dorota Gryko

Ministry of Science and Higher Education, 0132/DIA/2017/46, Katarzyna Orłowska

History

Email Address of Submitting Author

dorota.gryko@icho.edu.pl

Institution

Institute of Organic Chemistry, Polish Academy of Sciences

Country

Poland

ORCID For Submitting Author

0000-0002-5197-4222

Declaration of Conflict of Interest

no conflict of interests is decleared

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