Direct trifluoromethylthiolation of terminal alkynes mediated by a hypervalent trifluoromethylthio-iodine() reagent; boosting effect of fluorinated alcohol

The direct trifluoromethylthiolation of terminal alkynes is an important strategy for accessing CF 3 S-containing compounds. Herein, we report a direct trifluoromethylthiolation reaction of various terminal alkynes employing a new hypervalent trifluoromethylthio-iodine( iii ) reagent TFTI in a fluor...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2024-05, Vol.26 (1), p.5914-592
Main Authors: Cheng, Yu-Xin, Yang, Xiao-Guang, Du, Feng-Huan, Zhang, Chi
Format: Article
Language:English
Subjects:
Alcohols
Alkynes
Butanol
Fluorination
Green chemistry
Iodine
Propanol
Reaction mechanisms
Reagents
tert-Butanol
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Summary:The direct trifluoromethylthiolation of terminal alkynes is an important strategy for accessing CF 3 S-containing compounds. Herein, we report a direct trifluoromethylthiolation reaction of various terminal alkynes employing a new hypervalent trifluoromethylthio-iodine( iii ) reagent TFTI in a fluorinated alcohol, either 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) or perfluoro- tert -butanol (PFTB). The reaction mechanism is proposed on the basis of experiments and DFT calculations. The sustainability of TFTI and the recovery of PFTB make the reaction environmentally friendly. And, the protocol was found to be an excellent one in the context of green chemistry based on green chemistry metrics evaluation and EcoScale score. We reported a direct simple trifluoromethylthiolation reaction of various terminal alkynes using a new hypervalent trifluoromethylthio-iodine( iii ) reagent TFTI in a fluorinated alcohol, either hexafluoro-2-propanol or perfluoro- tert -butanol.
ISSN:1463-9262
1463-9270
DOI:10.1039/d4gc00622d