4.8 Article

Construction of Eight-Membered Cyclic Diaryl Sulfides via Domino Reaction of Arynes with Thioaurone Analogues and DFT Study on the Reaction Mechanism

Journal

ORGANIC LETTERS
Volume 21, Issue 22, Pages 9014-9018

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03417

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Funding

  1. National Natural Science Foundation of China [21403154]
  2. Natural Science Foundation of Tianjin [13JCYBJC38700]
  3. Tianjin Municipal Education Commission [2018KJ137]
  4. 131 Talents Program of Tianjin and Training Project of Innovation Team of Colleges and Universities in Tianjin [TD13-5020]

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Eight-membered cyclic and [5,5]-bicyclic sulfides were synthesized via a domino reaction between thioaurone analogues and arynes. Density functional theory calculations were performed to elucidate the reaction mechanism, which involves the elementary steps of the [3 + 2] cycloaddition, 1,2-hydrogen shift, and C(sp(2))-S bond cleavage as well as the substituent effect.

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