4.7 Article

Rhodium(III)-Catalyzed Oxadiazole-Directed Alkenyl C-H Activation for Synthetic Access to 2-Acylamino and 2-Amino Pyridines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 19, Pages 9978-9987

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01303

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Funding

  1. National Natural Science foundation of China [21425415, 21274058]
  2. National Basic Research Program of China [2015CB856303]

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We report herein a Rh(III)-catalyzed alkenyl CH activation protocol for the coupling of oxadiazoles with alkynes and synthesis of 2-acylamino and 2-amino pyridines, an important heterocyclic scaffold for various naturals products and synthetic pharmaceuticals bearing a readily reacting functional group. The selective protection/deprotection of amino groups through simple solvent switching, good functional group compatibility, superior product yield, and high regioselectivity are some of the notable synthetic features witnessed in this reaction protocol.

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