Synthesis of Multifluoromethylated γ-Sultines by a Photoinduced Radical Addition-Polar Cyclization.
Angew Chem Int Ed Engl
; 62(15): e202300159, 2023 Apr 03.
Article
em En
| MEDLINE
| ID: mdl-36762878
ABSTRACT
Despite the significance of sultines in synthesis, medicine, and materials science, the chemistry of sultines has remained unexplored due to their inaccessibility. Herein, we demonstrate the development of a photoredox-catalyzed multifluoromethyl radical addition/SO2 incorporation/polar cyclization cascade approach to multifluoromethylated γ-sultines. The reactions proceed by single electron transfer induced multifluoromethyl radical addition to an alkene followed by SO2 incorporation, and single-electron reduction for polar 5-exo-tet cyclization. Key to the success of the protocol is the use of easily oxidizable multifluoroalkanesulfinates as bifunctional reagents. The reactions proceed with excellent functional-group tolerance to deliver γ-sultines in moderate to excellent yields.
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MEDLINE
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En
Ano de publicação:
2023
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Article