Palladium-Catalyzed β-C-H Arylation of Alkyl Carboxamides with Sterically Hindered Aryl Iodides Using ortho-Sulfinyl Aniline Auxiliaries

Delong Mu, Fang Gao, Gong Chen, Gang He

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

We disclose a pair of ortho-sulfinylaniline auxiliaries for palladium-catalyzed β-C-H arylation of alkyl carboxamides. Together, these auxiliaries offer a means to effect efficient β-methyl and methylene C-H bond arylation with sterically hindered aryl iodides. ortho-Methylsulfinylaniline (MSOA) enables efficient β-methyl C-H arylation of propanamide substrates with aryl iodides bearing various ortho-substituents including alkyl groups. ortho-Tosylsulfinylaniline (TSOA) enables β-methylene C-H arylation with ortho-substituted aryl iodides. Both amide-linked MSOA and TSOA auxiliaries can be easily removed to give ester products under relatively mild conditions.

Original languageEnglish (US)
Pages (from-to)1880-1885
Number of pages6
JournalACS Catalysis
Volume7
Issue number3
DOIs
StatePublished - Mar 3 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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