A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl-Alkyl Cross-Coupling Reactions.
Published version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Greb, Andreas
Poh, Jian-Siang https://orcid.org/0000-0002-6173-8290
Greed, Stephanie
Battilocchio, Claudio https://orcid.org/0000-0002-4601-8527
Pasau, Patrick
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.
Description
Keywords
boronic acids, cross-coupling, diazo compounds, flow chemistry, photochemistry
Journal Title
Angew Chem Int Ed Engl
Conference Name
Journal ISSN
1433-7851
1521-3773
1521-3773
Volume Title
56
Publisher
Wiley
Publisher DOI
Sponsorship
Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/M004120/1)
European Commission Horizon 2020 (H2020) Future and Emerging Technologies (FET) (737266)
Engineering and Physical Sciences Research Council (EP/K039520/1)
Engineering and Physical Sciences Research Council (EP/M004120/1)
European Commission Horizon 2020 (H2020) Future and Emerging Technologies (FET) (737266)
Engineering and Physical Sciences Research Council (EP/K039520/1)
Pfizer
The Cambridge Home and EU Scholarship Scheme
UCB Biopharma SPRL