4.4 Article

K2S2O8-promoted radical trifluoromethylthiolation/spirocyclization for the synthesis of SCF3-featured spiro[5,5]trienones

Journal

TETRAHEDRON
Volume 106, Issue -, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.132649

Keywords

Trifluoromethylthiolation; Dearomatization; Radical cascade cyclization; Alkynes

Funding

  1. Natural Science Foundation of the Jiangsu Higher Education Institutions of China [19KJB150020]
  2. Basic Research Project (Natural Science Foundation for Young Scholars) of Jiangsu Province, China [BK20200953]

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A direct and efficient strategy for the trifluoromethylthiolation and dearomatization of biaryl ynones with stable and readily available AgSCF3 has been developed. The reaction occurs smoothly in the presence of K2S2O8 via a 6-exo-trig radical cyclization, providing a variety of SCF3-containing spiro [5,5] trienones in good yields.
A direct and efficient strategy for the trifluoromethylthiolation and dearomatization of biaryl ynones with stable and readily available AgSCF3 has been developed. The reaction occurs smoothly in the presence of K2S2O8 via a 6-exo-trig radical cyclization, providing a variety of SCF3-containing spiro [5,5] trienones in good yields. (C) 2022 Elsevier Ltd. All rights reserved.

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