Journal
ORGANIC LETTERS
Volume 22, Issue 2, Pages 615-619Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04389
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Funding
- National Natural Science Foundation [21772046, 2193103]
- Natural Science Foundation of Fujian Province [2016J01064]
- Subsidized Project for Cultivating Postgraduates' Innovative Ability in Scientific Research of Huaqiao University
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A divergent strategy for precise construction of SCF2H or SeCF2H groups on heteroarenes generated in situ from CF3-containing 1,3-enynes was developed. Reactions of readily available 1,3-enynes with S-8 and ClCF2H provided 3-SCF2H-4-CF3-thiophenes via a cascade thiophene construction/selective C3 position thiolation/difluoromethylthiolation process, as did a series of 3-SeCF2H-4-CF3-selenophenes by similar strategies. The plausible radical annulation process for the construction of the thiophene ring and difluorocarbene generated in situ was confirmed by experiment.
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