Journal
ORGANIC LETTERS
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03327
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- Japan Society for the Promotion of Science (JSPS) [JP 20H04824, 21H01941, 22H05370]
- Japan Science and Technology Agency (JST) [JPMJSP2136]
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The first example of 3-position-selective C(sp2)-H trifluoromethylation of pyridine rings was successfully achieved. This reaction can be used for perfluoroalkylation at the 3 position of pyridine rings and late-stage trifluoromethylation of bioactive molecules.
The first example of the 3-position-selective C(sp2)-H trifluoromethylation of pyridine rings was established. 3-Position selective trifluoromethylation was achieved by the nucleophilic activation of pyridine and quinoline derivatives through hydrosilylation and successive electrophilic trifluoromethylation of the enamine intermediate. This reaction was applicable to perfluoroalkylation at the 3 position of the pyridine rings and late-stage trifluoromethylation of a bioactive molecule. Mechanistic studies indicated that the reaction proceeds via the formation of N-silyl enamine and trifluoromethylated enamine intermediates.
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