4.8 Article

Switchable Copper-Catalyzed Approach to Benzodithiole, Benzothiaselenole, and Dibenzodithiocine Skeletons

Journal

ORGANIC LETTERS
Volume 22, Issue 9, Pages 3454-3459

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00907

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Funding

  1. National Natural Science Foundation of China [21772070, 21702078]
  2. Natural Science Foundation of the Jiangsu Higher Education Institution [17KJA150003]
  3. KTH Royal Institute of Technology
  4. Wenner-Gren Foundations
  5. Olle Engkvist Foundation

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A copper-catalyzed reaction between 2-bromo-benzothioamides and S-8 or Se involving sulfur rearrangement is reported, enabling access to benzodithioles 2 and benzothiaselenoles 6 in the presence of Cs2CO3. In the absence of S8 or Se, the reaction affords dibenzodithiocines 7 via two consecutive C(sp(2))-S Ullmann couplings.

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