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Dehydration in water: frustrated Lewis pairs directly catalyzed allylization of electron-rich arenes and allyl alcohols.

ABSTRACT: A frustrated Lewis pair (FLP)-catalyzed allylation of allyl alcohols with electron-rich arenes has been developed. Interestingly, in this reaction, the electron-rich arenes and allyl alcohols are dehydrated in water. What's more, water was the sole byproduct of the reaction. In this protocol, various allyl alcohols can be converted into allyl cations and attacked by the electron-rich arenes to form aryl cation intermediates. Finally, the aryl cation intermediates are deprotonated to give the 1,3-diarylpropenes. In this protocol, indole allyl alcohols can undergo a bimolecular ring closure reaction, and structurally diverse tetrahydroindolo[3,2-b]carbazoles could be smoothly obtained. The reaction is not sensitive to oxygen and has been performed on a gram-scale.

SUBMITTER: Zhang H

PROVIDER: S-EPMC9053410 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Dehydration in water: frustrated Lewis pairs directly catalyzed allylization of electron-rich arenes and allyl alcohols.

Zhang Hua H Zhan Xiao-Yu XY Dong Yu Y Yang Jian J He Shuai S Shi Zhi-Chuan ZC Zhang Xiao-Mei XM Wang Ji-Yu JY

RSC advances 20200430 29

A frustrated Lewis pair (FLP)-catalyzed allylation of allyl alcohols with electron-rich arenes has been developed. Interestingly, in this reaction, the electron-rich arenes and allyl alcohols are dehydrated in water. What's more, water was the sole byproduct of the reaction. In this protocol, various allyl alcohols can be converted into allyl cations and attacked by the electron-rich arenes to form aryl cation intermediates. Finally, the aryl cation intermediates are deprotonated to give the 1,3 ...[more]

PMID: 35521451

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