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Visible-Light-Antenna Ligand-Enabled Samarium-Catalyzed Reductive Transformations.

Takahito Kuribara1,2, Ayahito Kaneki2, Yu Matsuda2

  • 1Institute for Advanced Academic Research, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

Journal of the American Chemical Society
|July 20, 2024
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Summary
This summary is machine-generated.

This study introduces a novel samarium (Sm) catalyst with a visible-light antenna ligand for efficient reductive transformations. The catalyst enables mild conditions for pinacol coupling and various other single-electron reduction reactions.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Photochemistry

Background:

  • Divalent samarium (Sm) reagents are crucial for single-electron transfer in reductive transformations.
  • Catalytic applications of Sm reagents are often challenging due to stability and reactivity issues.
  • Developing mild and efficient Sm-catalyzed reactions is an ongoing area of research.

Purpose of the Study:

  • To design a novel ligand for samarium-catalyzed reduction reactions.
  • To achieve mild reaction conditions using visible-light irradiation.
  • To expand the scope of samarium-catalyzed single-electron reductive transformations.

Main Methods:

  • Design of a bidentate phosphine oxide ligand with a 9,10-diphenylanthracene visible-light antenna.
  • Development of samarium-catalyzed pinacol coupling of aryl ketones and aldehydes using 1 mol % Sm catalyst.
  • Utilizing an organic amine (DIPEA) as a sacrificial mild reductant.
  • Investigating the reaction mechanism through mechanistic studies.

Main Results:

  • Successful development of a catalytic system for pinacol coupling under mild conditions.
  • Demonstration of the ligand's role in reducing Sm(III) to Sm(II) via visible-light irradiation.
  • Expansion of the catalytic system to various single-electron reductive transformations, including cross-pinacol coupling, aza-pinacol coupling, flavone dimerization, C-O bond cleavage, C-C ring-opening of cyclopropane, ketyl-olefin coupling, and cross-coupling of ketyl and α-amino radicals.

Conclusions:

  • A novel visible-light-antenna ligand enables efficient samarium-catalyzed reductive transformations under mild conditions.
  • The developed catalytic system broadens the applicability of samarium in organic synthesis.
  • This approach offers a new strategy for utilizing light in samarium-mediated single-electron transfer reactions.