4.6 Article

Copper-catalyzed cascade click/nucleophilic substitution reaction to access fully substituted triazolyl-organosulfurs

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 46, Pages 9933-9941

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob02081k

Keywords

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Funding

  1. National Natural Science Foundation of China [21978039, 21702025]
  2. Science and Technology Innovation Foundation of Dalian City [2019J12GX029]
  3. Fundamental Research Funds for the Central Universities [DUT18LK25]

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A novel cascade click/nucleophilic substitution reaction is developed to access 4-heterofunctionalized fully substituted triazolyl-organosulfurs using thiocyanates as both leaving groups and organosulfur precursors. This method features high regioselectivities and board substrate scope. 33 examples are shown to demonstrate the structural diversity through the synthesis of fully substituted triazolyl-organosulfurs including triazolyl-thiocyanates, triazolyl-sulfinylcyanides, triazolyl-thioethers, triazolyl-thiols and triazolyl-disulfides from internal thiocyanatoalkynes.

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