期刊
CHEMICAL COMMUNICATIONS
卷 59, 期 26, 页码 3862-3865出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc06967a
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In this study, an intramolecular endo-selective Heck reaction of iodomethylsilyl ethers of phenols and alkenols was reported. The reaction resulted in the formation of seven- and eight-membered siloxycycles in excellent yields, which could be further converted into the corresponding allylic alcohols upon oxidation. This method could be used for the selective (Z)-hydroxymethylation of o-hydroxystyrenes and alkenols. Rapid scan EPR experiments and DFT calculations suggested a concerted beta-hydrogen elimination event to take place in the triplet state.
Herein, we report an intramolecular endo-selective Heck reaction of iodomethylsilyl ethers of phenols and alkenols. The reaction leads to the formation of seven- and eight-membered siloxycycles in excellent yields, which could be further converted into the corresponding allylic alcohols upon oxidation. Thus, this method could be used for the selective (Z)-hydroxymethylation of o-hydroxystyrenes and alkenols. Rapid scan EPR experiments and DFT calculations suggest a concerted beta-hydrogen elimination event to take place in the triplet state.
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