Distal -C-H functionalization of α-substituted cinnamates

Development of a novel strategy for the palladium-catalyzed selective meta -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, maleimide...

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Published inChemical science (Cambridge) Vol. 14; no. 22; pp. 588 - 5886
Main Authors Bakthadoss, Manickam, Reddy, Tadiparthi Thirupathi
Format Journal Article
Published 07.06.2023
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Summary:Development of a novel strategy for the palladium-catalyzed selective meta -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 meta -C-H activation reaction for the first time. Notably, allylation, acetoxylation and cyanation were also achieved through distal meta -C-H functionalization. This novel protocol also includes the coupling of various olefin-tethered bioactive molecules with high selectivity. Distal meta -selective C-H olefination, allylation, acetoxylation and cyanation of α-substituted cinnamates have been reported. New coupling partners such as quinones, maleimides and sulfolene were utilized for the first time in meta -C-H activation.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
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2213840
2213839
https://doi.org/10.1039/d2sc06206b
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2213838
ISSN:2041-6520
2041-6539
DOI:10.1039/d2sc06206b