Issue 46, 2019

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
25 Sep 2019
Accepted
07 Nov 2019
First published
07 Nov 2019

Org. Biomol. Chem., 2019,17, 9933-9941

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

M. Li, K. Dong, Y. Zheng and W. Song, Org. Biomol. Chem., 2019, 17, 9933 DOI: 10.1039/C9OB02081K

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