Distal meta -C-H functionalization of α-substituted cinnamates

Development of a novel strategy for the palladium-catalyzed selective -C-H activation of α-substituted cinnamates and their heterocyclic analogues with various alkenes using nitrile as a directing group (DG) has been described. Importantly, we introduced naphthoquinone, benzoquinones, maleimides and...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2023-06, Vol.14 (22), p.5880-5886
Main Authors: Bakthadoss, Manickam, Reddy, Tadiparthi Thirupathi
Format: Article
Language:English
Subjects:
Allyl compounds
Chemical reactions
Chemistry
Coupling (molecular)
Palladium
Substitutes
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Summary:Development of a novel strategy for the palladium-catalyzed selective -C-H activation of α-substituted cinnamates and their heterocyclic analogues with various alkenes using nitrile as a directing group (DG) has been described. Importantly, we introduced naphthoquinone, benzoquinones, maleimides and sulfolene as coupling partners in the -C-H activation reaction for the first time. Notably, allylation, acetoxylation and cyanation were also achieved through distal -C-H functionalization. This novel protocol also includes the coupling of various olefin-tethered bioactive molecules with high selectivity.
ISSN:2041-6520
2041-6539
DOI:10.1039/d2sc06206b