4.7 Article

Metal-Free Photochemical C-Se Cross-Coupling of Aryl Halides with Diselenides

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 9, Pages 1607-1612

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200042

Keywords

Aryl halides; Diselenides; Photochemistry; Radical reactions; C-Se bond coupling

Funding

  1. National Natural Science Foundation of China [21602169, 81803490]
  2. China Postdoctoral Science Foundation [2016M592775]
  3. Xi'an Jiaotong University [334100038]

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A light-mediated C-Se bond coupling reaction between aryl halides and diselenides has been achieved under mild and photocatalyst-free conditions, resulting in the synthesis of aryl selenoethers. The transformation offers readily available materials, mild reaction conditions, a broad substrate scope, and high efficiency. A plausible mechanism has been proposed based on the initial mechanistic investigation, and the protocol is also applicable for forging C-S and C-Te bonds using disulfides and ditellurides.
A light-mediated C-Se bond coupling reaction of aryl halides with diselenides under mild photocatalyst-free conditions for preparing aryl selenoethers has been achieved. The transformation is charactered by readily available materials, mild conditions, broad substrate scope and high efficiency. A reasonable mechanism has been proposed based on the preliminary mechanistic investigation. The protocol is also suitable for forging C-S bond and C-Te bond by the use of disulfides and ditellurides.

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