4.7 Article

Iron-Catalyzed Silylation and Spirocyclization of Biaryl-Ynones: A Radical Cascade Process toward Silylated Spiro[5.5]trienones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 9, Pages 1537-1542

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200049

Keywords

silylation silylated spiro [5.5]trienones; spirocyclization; alkynes; iron-catalysis; radical reactions

Funding

  1. National Natural Science Foundation of China [22001012, 21901006]
  2. Foundation of Henan Educational Committee [21A150008, 20B150003]
  3. Foundation of Henan Science and Technology Department [212102311061]
  4. Foundation of Anyang Science and Technology Bureau [ZK2021C01GX016]
  5. Foundation of Anyang Normal University [AYNUKPY-2019-08, AYNUKPY-2019-10]

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In this study, an iron-catalyzed cascade reaction was developed for the synthesis of silylated spiro[5.5]trienones using silane as the precursor of silyl radical. The approach involved 1,10-phenanthroline as the ligand and tert-butyl hydroperoxide (TBHP) as the oxidant, leading to the formation of silylated compounds.
Iron-catalyzed cascade silyl radical addition/6-exo-trig cyclization/dearomatization of biaryl ynones has been developed. This approach uses silane as the precursor of silyl radical as well as silylation reagent, 1,10-phenanthroline as the ligand, and tert-butyl hydroperoxide (TBHP) as the oxidant. By employing this tandem process, a series of silylated spiro[5.5]trienones were prepared.

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