Methylene C(sp3)–H β,β′-Diarylation of Cyclohexane­carbaldehydes Promoted by a Transient Directing Group and Pyridone Ligand

A hindered β-amino amide transient directing group effects di-trans-arylation of cyclohexanecarbaldehydes. The amide N-substituents are shown to affect yield and can enhance the rate of arylation compared with the α-amino acid. Addition of a pyridone ligand further enhanced reactivity. The reaction...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 5; pp. 1807 - 1812
Main Authors St John-Campbell, Sahra, White, Andrew J. P, Bull, James A
Format Journal Article
LanguageEnglish
Published American Chemical Society 06.03.2020
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Summary:A hindered β-amino amide transient directing group effects di-trans-arylation of cyclohexanecarbaldehydes. The amide N-substituents are shown to affect yield and can enhance the rate of arylation compared with the α-amino acid. Addition of a pyridone ligand further enhanced reactivity. The reaction is successful for a range of aryl iodides, and various substituted cyclohexane carboxaldehydes, providing functionalized products from simple feedstocks. A mechanism is proposed evoking a transient enamine.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00124