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A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl–Alkyl Cross‐Coupling Reactions
Author(s) -
Greb Andreas,
Poh JianSiang,
Greed Stephanie,
Battilocchio Claudio,
Pasau Patrick,
Blakemore David C.,
Ley Steven V.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201710445
Subject(s) - diazo , chemistry , aryl , alkyl , functional group , combinatorial chemistry , photodissociation , coupling (piping) , photochemistry , computational chemistry , organic chemistry , materials science , polymer , metallurgy
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(sp 2 )−C(sp 3 ) cross‐coupling processes, with excellent functional‐group tolerance.