4.4 Article

Carbon radical addition-cyclization reaction induced by ruthenium-photocatalyst under visible light irradiation

Journal

TETRAHEDRON
Volume 71, Issue 5, Pages 773-781

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.12.068

Keywords

Radical; Photochemistry; Catalysis; Perfluoroalkyl; Trifluoromethyl

Funding

  1. Japan Society for the Promotion of Science KAKENHI [25460028]
  2. Grants-in-Aid for Scientific Research [24790032, 25460028] Funding Source: KAKEN

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In the presence of Ru(bpY)(3)Cl-2 center dot 6H(2)O and (i-Pr)(2)NEt, the photo-induced cascade radical addition -cyclization-trapping reaction proceeded in aqueous media. When i-C3F7I was employed as a radical precursor, the iodine atom-transfer radical cyclization proceeded even in the absence of (i-Pr)(2)NEt. Under the photo-induced conditions, ICH2CN and ICH2CF3 also worked well as carbon radical precursors. The photo-induced reductive electron-transfer to CF3SO2Cl promoted the chlorine atom-transfer radical cyclization. (C) 2014 Elsevier Ltd. All rights reserved.

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