4.7 Article

Hexafluoroisopropanol-Mediated Redox-Neutral α-C(sp3)-H Functionalization of Cyclic Amines via Hydride Transfer

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 4, Pages 1915-1926

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02606

Keywords

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Funding

  1. Taishan Scholars Construction Projects of Shandong [tsqn201909131]
  2. NSFC [21878167]
  3. Natural Science Foundation of Shandong Province [JQ201604]
  4. Key Research and Development Program of Shandong Province [2017GSF218073]
  5. Qingdao Special Research Foundation of Science and Technology [19-6-1-38-nsh]

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Hexafluoroisopropanol has been demonstrated as the versatile promoter for redox-neutral alpha-C(sp(3))-H functionalization of cyclic amines via the cascade [1,5]-hydride transfer/cyclization strategy. A wide range of cyclic amines are functionalized into bioactive tetrahydroquinolines, quinazolines, benzoxazines, and benzotriazepines in moderate to excellent yields. This protocol features additive-free conditions, operational simplicity, and wide substrate scope.

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