Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 41, Pages 14324-14327Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502914
Keywords
electrophilic substitution; fluorine; fluoroalkylthiolation; sulfur; synthetic methods
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Funding
- Nanokat
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An AlCl3-catalyzed C-H thiocyanation was discovered and combined with a Langlois-type trifluoromethylation to afford aryl trifluoromethyl thioethers directly from arenes, N-thiocyanatosuccinimide (NTS) and Ruppert-Prakash reagent. An analogous combination with a copper-mediated difluoromethylation gives access to aryl difluoromethyl thioethers. Both processes proceed with exceptional regioselectivity for the most electron-rich, sterically least hindered position of the arene. The sulfur and fluoroalkyl groups originate from different sources, so that the use of expensive, preformed fluoroalkylthiolation reagents is avoided.
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