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- Title
A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl-Alkyl Cross-Coupling Reactions.
- Authors
Greb, Andreas; Poh, Jian‐Siang; Greed, Stephanie; Battilocchio, Claudio; Pasau, Patrick; Blakemore, David C.; Ley, Steven V.
- Abstract
Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon-carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and the scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp2)−C(sp3) cross-coupling processes, with excellent functional-group tolerance.
- Subjects
DIAZO compounds; BORONIC acids; COUPLING reactions (Chemistry); OXADIAZOLINES; CHEMICAL precursors; CARBON-carbon bonds; FLOW chemistry; ULTRAVIOLET photolysis
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 52, p16829
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201710445