4.7 Article

The cobalt(ii)-catalyzed acyloxylation of picolinamides with bifunctional silver carboxylate via C-H bond activation

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 19, Pages 5125-5132

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01131j

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Funding

  1. Key-Area Research and Development Program of Guangdong Province [2020B010188001]
  2. Guangdong Basic and Applied Basic Research Foundation [2021A1515110160]

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A cobalt(ii)-catalyzed C-H bond acyloxylation of picolinamides with bifunctional silver carboxylate has been developed. This operationally simple acyloxylation allows for efficient synthesis of 8-functionalized 1-naphthylamine under mild conditions without the need for additional oxidants and base additives. The mild and practical acyloxylation approach provides a pathway for accessing highly functionalized polysubstituted naphthalene compounds and for modifying drug molecules and natural products.
The cobalt(ii)-catalyzed C-H bond acyloxylation of picolinamides with bifunctional silver carboxylate has been developed. The operationally simple acyloxylation allowed us to efficiently synthesize 8-functionalized 1-naphthylamine (up to 94% yield) under mild conditions without any additional oxidant and base additives. Control experiments were performed to investigate the mechanism of the reaction. This mild and practical acyloxylation approach provides an efficient route for accessing highly functionalized polysubstituted naphthalene compounds and a pathway for modifying drug molecules and natural products.

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