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

Research output: Contribution to journalArticle

254 Citations (Scopus)

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

Fingerprint

Alkylation
Palladium
Iodides
Amines
Catalysis
Phosphates
Substrates
picolinamide

All Science Journal Classification (ASJC) codes

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

Cite this

Zhang, Shu Yu ; He, Gang ; Nack, William A. ; Zhao, Yingsheng ; Li, Qiong ; Chen, Gong. / Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 6. pp. 2124-2127.
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Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides. / Zhang, Shu Yu; He, Gang; Nack, William A.; Zhao, Yingsheng; Li, Qiong; Chen, Gong.

In: Journal of the American Chemical Society, Vol. 135, No. 6, 13.02.2013, p. 2124-2127.

Research output: Contribution to journalArticle

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T1 - Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides

AU - Zhang, Shu Yu

AU - He, Gang

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AU - Li, Qiong

AU - Chen, Gong

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