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Copper-catalyzed cascade click/nucleophilic substitution reaction to access fully substituted triazolyl-organosulfurs using thiocyanates as both leaving groups and organosulfur precursors

Abstract

Although Cu(I)-catalyzed electrophilic interrupted click reaction where 5-cuprate-triazole is trapped by various electrophiles in inter- or intramolecular manner has been well-documented, highly reactive electrophiles are still required to avoid the parasitic protonation for electrophilic interrupted click reaction. Herein, we developed a novel cascade click/nucleophilic substitution reaction to access 4-heterofunctionalized fully substituted triazolyl-organosulfurs using thiocyanates as both leaving groups and organosulfur precursors. 33 examples are showed 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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Publication details

The article was received on 25 Sep 2019, accepted on 07 Nov 2019 and first published on 07 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02081K
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Copper-catalyzed cascade click/nucleophilic substitution reaction to access fully substituted triazolyl-organosulfurs using thiocyanates as both leaving groups and organosulfur precursors

    M. Li, K. Dong, Y. Zheng and W. Song, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB02081K

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