Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides

Shu Yu Zhang, Gang He, William A. Nack, Yingsheng Zhao, Qiong Li, Gong Chen

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281 Scopus citations

Abstract

We report an efficient method for the alkylation of γ-C(sp 3)-H bonds of picolinamide-protected aliphatic amine substrates with primary alkyl iodides via palladium catalysis. Ag2CO3 and dibenzyl phosphate, (BnO)2PO2H, are critical promoters of this reaction. These reactions provide a convenient and straightforward method for the preparation of high-value N-containing products from readily available amine and alkyl iodide precursors.

Original languageEnglish (US)
Pages (from-to)2124-2127
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number6
DOIs
StatePublished - Feb 13 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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