期刊
ORGANIC LETTERS
卷 23, 期 19, 页码 7376-7380出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02552
关键词
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资金
- Spanish Agencia Estatal de Investigacion [PID2019-110037GB-I00, PCI2019111933-2]
- European Union's Horizon 2020 (FET-Open project) [863098]
- Xunta de Galicia [ED431C 2020/22]
- Xunta de Galicia (Centro Singular de Investigacion de Galicia accreditation 2019-2022) [ED431G 2019/03]
- European Union (European Regional Development Fund ERDF)
- European Union (European Social Fund, ESF)
A complex mechanism involving the generation of an intermediate ketocarbene, which adds to the cyclopentadienone to give an isolable tricyclic intermediate, followed by thermal rearrangements, is proposed to explain the formation of the product in the reaction of 2-(trimethylsilyl)thiophen-3-yl triflate with CsF in the presence of 2,3,4,5-tetraphenylcyclopentadienone. The intermediacy of the hypothesized 5-membered hetaryne is discarded based on detailed experimental and computational studies, suggesting a different pathway for the reaction.
The reaction of 2-(trimethylsily)thiophen-3-yl triflate with CsF in the presence of 2,3,4,5-tetraphenylcyclopentadienone affords 4,5,6,7-tetraphenylbenzo[b]thiophene, as it would be expected from the hypothesized generation and trapping of 2-thiophyne. However, a detailed experimental and computational study discards the intermediacy of this elusive 5-membered hetaryne. Instead, a complex mechanism involving the generation of an intermediate ketocarbene, which adds to the cyclo-pentadienone to give an isolable tricyclic intermediate, followed by thermal rearrangements, is proposed.
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