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Four-Component Radical 1,2-Selenosulfonylation of Allenes.

Xiao-Rong Shu1, Mu-Han Li1, Cuiyan Wu2,3

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|June 27, 2024
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This study introduces an iron-catalyzed reaction for synthesizing complex selenosulfones from allenes. The novel method efficiently creates two C-S and one C-Se bond in a single step, offering a greener approach to these vital pharmaceutical compounds.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Selenosulfones are crucial structural motifs in pharmaceuticals.
  • Efficient synthesis of selenosulfones is a key challenge in organic synthesis.
  • Radical reactions offer versatile pathways for C-S and C-Se bond formation.

Purpose of the Study:

  • To develop a novel, efficient, and eco-friendly method for synthesizing complex selenosulfones.
  • To achieve the 1,2-selenosulfonylation of allenes via a controllable radical tandem reaction.
  • To explore the scope and applicability of the developed synthetic methodology.

Main Methods:

  • An iron-catalyzed four-component radical tandem reaction was employed.
  • Reactants included allenes, cycloketone oxime esters, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), and diphenyl diselenides.
  • Reaction conditions were optimized for mildness, efficiency, and regioselectivity.

Main Results:

  • The first reported 1,2-selenosulfonylation of allenes using a radical process was achieved.
  • The reaction demonstrated high regioselectivity due to controlled radical rates and polarity matching.
  • The one-pot procedure efficiently formed two new C-S bonds and one C-Se bond.
  • The methodology was extended to utilize aryldiazonium tetrafluoroborates as an alternative substrate.

Conclusions:

  • A novel and efficient iron-catalyzed four-component reaction for selenosulfone synthesis has been established.
  • The developed method provides a regioselective and step-efficient route to complex selenosulfones.
  • This work expands the synthetic utility of allenes in radical chemistry for pharmaceutical applications.