Palladium-catalyzed picolinamide-directed acetoxylation of unactivated γ-C(sp3)-H bonds of alkylamines

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

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

We report a new protocol for palladium-catalyzed acetoxylation of the γ-C(sp3)-H bonds of N-alkylpicolinamide substrates using PhI(OAc)2 oxidant. These reactions involve the use of substoichiometric amounts of Li2CO3 additive, which effectively suppresses the competing intramolecular C-H amination process. Under these conditions, N-propylpicolinamides bearing α substituents can be cleanly converted to γ-acetoxylated amine products in excellent yield. This C-H acetoxylation can also be used in concert with other Pd-catalyzed picolinamide-directed C-H functionalization reactions for rapid scaffold diversification.

Original languageEnglish (US)
Pages (from-to)1544-1548
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number7
DOIs
StatePublished - May 5 2014

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Bearings (structural)
Amination
Palladium
Oxidants
Scaffolds
Amines
Substrates
picolinamide

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Li, Qiong ; Zhang, Shu Yu ; He, Gang ; Nack, William A. ; Chen, Gong. / Palladium-catalyzed picolinamide-directed acetoxylation of unactivated γ-C(sp3)-H bonds of alkylamines. In: Advanced Synthesis and Catalysis. 2014 ; Vol. 356, No. 7. pp. 1544-1548.
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Palladium-catalyzed picolinamide-directed acetoxylation of unactivated γ-C(sp3)-H bonds of alkylamines. / Li, Qiong; Zhang, Shu Yu; He, Gang; Nack, William A.; Chen, Gong.

In: Advanced Synthesis and Catalysis, Vol. 356, No. 7, 05.05.2014, p. 1544-1548.

Research output: Contribution to journalArticle

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