Ester-directed orthogonal dual C-H activation and ortho aryl C-H alkenylation via distal weak coordination

An unprecedented orthogonal cross-coupling between aromatic C(sp ) and aliphatic olefinic C(sp ) carbons of two same molecules dual C-H bond activation in an intermolecular fashion has been developed using a distal ester-directing group. This new coupling reaction led to the synthesis of the highly...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 58; no. 9; pp. 1406 - 1409
Main Authors Bakthadoss, Manickam, Reddy, Tadiparthi Thirupathi, Agarwal, Vishal, Sharada, Duddu S
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 27.01.2022
Subjects
Acrylates
Alkenes
Aromatic compounds
Chemical synthesis
Coupling (molecular)
Cross coupling
Esters
Hydrogen bonds
Molecular structure
Substrates
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Summary:An unprecedented orthogonal cross-coupling between aromatic C(sp ) and aliphatic olefinic C(sp ) carbons of two same molecules dual C-H bond activation in an intermolecular fashion has been developed using a distal ester-directing group. This new coupling reaction led to the synthesis of the highly functionalized 1,3-diaryl molecular architecture in very good yields and with high chemo- and regioselectivities. In addition, using ester as the distal directing group, C-H olefination of α-methyl aryl acrylates and cinnamic esters with various alkenes has been achieved in very good yields and with a wide range of substrate scope.
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ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06097j