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A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl-Alkyl Cross-Coupling Reactions.

Published version
Peer-reviewed

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Type

Article

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Authors

Greb, Andreas 
Greed, Stephanie 
Battilocchio, Claudio  ORCID logo  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

Volume Title

56

Publisher

Wiley
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)
Pfizer The Cambridge Home and EU Scholarship Scheme UCB Biopharma SPRL