Palladium-catalyzed ortho-C(sp2)H bromination of benzaldehydes via a monodentate transient directing group strategy

[Display omitted] •An efficient monodentate transient directing group strategy was developed.•ortho-CH bromination of benzaldehydes was catalyzed by Pd via Monodentate TDG.•Mild reaction conditions and no addition of silver salt are featured. A facile and efficient monodentate transient directing gr...

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Bibliographic Details
Published in:Tetrahedron letters 2019-11, Vol.60 (46), p.151263, Article 151263
Main Authors: Yong, Qiyun, Sun, Bing, Zhang, Fang-Lin
Format: Article
Language:English
Subjects:
Benzaldehyde
Monodentate
Palladium
Transient directing group
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Summary:[Display omitted] •An efficient monodentate transient directing group strategy was developed.•ortho-CH bromination of benzaldehydes was catalyzed by Pd via Monodentate TDG.•Mild reaction conditions and no addition of silver salt are featured. A facile and efficient monodentate transient directing group strategy was developed to enable the palladium-catalyzed ortho-C(sp2)H bromination of benzaldehydes. A broad scope of benzaldehydes were transformed into the desired products by employing 2-amino-5-chlorobenzotrifluoride as a monodentate transient directing group, demonstrating good functional group tolerance. Mild reaction conditions and no requirement for a silver salt are also features of this strategy.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151263