4.7 Article

Simple Tandem Olefin Isomerization/Intramolecular Hydroamination of Alkenyl Amines with Various Allylic Tethers

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 17, Pages 11919-11924

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01640

Keywords

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Funding

  1. National Research Foundation of Korea (NRF) - Korean government (MSIT) [2020R1A6A1A06046728, 2021R1A5A6002803, 2021R1A2C1003135]
  2. National Research Foundation of Korea [2021R1A2C1003135] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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A simple and efficient one-pot process for the synthesis of diverse 2-alkyl-substituted 1,3-X,N-heterocycles through tandem olefin isomerization/intramolecular hydroamination has been developed. The process utilizes AgOTf catalyst and offers advantages such as high chemical yields, good functional group tolerance, and broad substrate scope.
A simple and efficient AgOTf-promoted tandem olefin isomerization/intramolecular hydroamination of 1,1-disub-stituted alkenyl amines has been developed. This one-pot process represents a facile and attractive route for the synthesis of diverse 2-alkyl-substituted 1,3-X,N-heterocycles through chemo-and regiose-lective C(sp3)-N bond formation with atom economy. Advantages such as the operationally simple and practical procedure that uses a readily available catalyst under aerobic conditions, good to excellent chemical yields, the high functional group tolerance, the broad substrate scope, and high efficiency and selectivity are noteworthy.

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