Gold‐Catalyzed Oxygen Transfer to Alkynylsulfones: A Diazo‐Free Route to 4‐Sulfonyl‐1,3‐Oxazoles

The gold‐catalyzed annulation of alkynylsulfones, involving pyridine N‐oxides (as O‐atom transfer reagents) and nitriles (as C=N synthons), comprises a diazo‐free route to valuable 4‐sulfonyl‐1,3‐oxazoles. This reaction operates under relatively mild conditions (IPrAuNTf2 5 mol %, rt or 60 °C), and...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-11, Vol.364 (21), p.3697-3707
Main Authors: Chikunova, Elena I., Dar'in, Dmitry V., Kukushkin, Vadim Yu, Dubovtsev, Alexey Yu
Format: Article
Language:English
Subjects:
1,3-Oxazoles
Chemical reactions
Gold
Gold catalysis
Homogeneous catalysis
Nitriles
Oxidation
Oxygen transfer
Reaction mechanisms
Reagents
Synthetic methods
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Summary:The gold‐catalyzed annulation of alkynylsulfones, involving pyridine N‐oxides (as O‐atom transfer reagents) and nitriles (as C=N synthons), comprises a diazo‐free route to valuable 4‐sulfonyl‐1,3‐oxazoles. This reaction operates under relatively mild conditions (IPrAuNTf2 5 mol %, rt or 60 °C), and a number of functionalities was compatible (35 examples; 14–95%). In most cases, the SO2 fragment, which is typically expulsed in the previously reported Au‐catalyzed O‐transfers to alkynylsulfones, retains in the heterocyclic products. The postulated reaction mechanism suggests a key role of reactive gold α‐oxo carbene intermediates formed via the O‐atom transfer.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200751