10.1002/ejoc.201800451
European Journal of Organic Chemistry
COMMUNICATION
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N
DG
SCF3
DG
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SCF3
R
N
Pd
2
R
SCF3
C
[6]
Scheme 6. Plausible mechanism.
Conclusions
In summary, we have developed an efficient palladium catalyzed
trifluoromethylthiolation of chelation assisted C-H bond of arenes.
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The
reaction
utilizes
the
readily
accessible
trifluoromethylthiolating reagent and various directing group like
pyridine, pyrimidine, pyrazole, quinoline and isoquinoline. This
also allows the synthesis of various trifluoromethylthiolated
arenes in good to excellent yield. Synthetic application was
demonstrated through ready conversion to sulfoxide and sulfone.
Furthermore, preliminary mechanistic investigation was
performed to understand the in-sight of the reaction mechanism.
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Acknowledgements
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We thank Indian Institute of Technology Madras (Project No.
CHY/16-17/840/RFIR/ANBA) for financial support. A.K. thanks
IIT Madras and M.C. thank Council of Scientific & Industrial
Research (CSIR) for a fellowship.
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Keywords: trifluoromethylthiolation • C-H bond functionalization
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