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Synfacts 2014; 10(9): 0961
DOI: 10.1055/s-0034-1378976
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Trifluoromethylthiolation

Contributor(s):
Paul Knochel
,
Jeffrey M. Hammann
Chen C, Xu X.-H, Yang B, Qing F.-L * Shanghai Institute of Organic Chemistry and Donghua University, Shanghai, P. R. of China
Copper-Catalyzed Direct Trifluoromethylthiolation of Benzylic C–H Bonds via Nondirected Oxidative C(sp3)–H Activation.

Org. Lett. 2014;
16: 3372-3375
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Further Information

Publication History

Publication Date:
18 August 2014 (online)

 
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Key words

copper - trifluoromethyl-thiolation - C–H activation

Significance

A copper-catalyzed trifluoromethyl­thiolation of benzylic C(sp3)–H bonds is described. The non-directed C–H activation using readily prepared and stable AgSCF3 leads to various benzyl trifluoromethyl sulfides in moderate to excellent yields.


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Comment

In this novel transformation, t-BuOOC(O)C6H4-3-CF3 was used as the oxidant and AgSCF3/KCl was used as the active trifluoromethylthio source.


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