4.8 Article

Bronsted Base-Modulated Regioselective Pd-Catalyzed Intramolecular Aerobic Oxidative Amination of Alkenes: Formation of Seven-Membered Amides and Evidence for Allylic C-H Activation

Journal

ORGANIC LETTERS
Volume 11, Issue 12, Pages 2707-2710

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900941t

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Funding

  1. Chinese Academy of Science
  2. National Natural Science Foundation of China [20821002, 20872155]
  3. National Basic Research Program of China [73-2009CB825300]
  4. Shanghai Municipality [08PJ1411600]

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A novel palladium-catalyzed intramolecular aerobic oxidative allylic C-H amination of olefins has been developed. Bronsted base can modulate the regioselectivity, favoring the formation of 7-membered rings. Mechanistic studies using deuterium-labeled substrates as probes support a rate-determining allylic C-H activation/irreversible reductive elimination pathway.

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