4.8 Article

Oxyamination of Unactivated Alkenes with Electron-Rich Amines and Acids via a Catalytic Triiodide Intermediate

Journal

ORGANIC LETTERS
Volume 22, Issue 3, Pages 884-890

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04432

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Funding

  1. University of Toledo

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An aerobic catalytic oxidation process is described for the olefin oxyamination using acids and primary amines as the sources of O and N. Our mechanistic findings point to the formation of triiodide as a critical catalytic intermediate to account for the tolerance of electron-rich nucleophiles. This dual iodide and copper catalytic system is suitable for a formal [5+1] annulation process to access valuable lactam structures and highlighted by the synthesis of the pharmaceutical Zamifenacin.

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