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镍催化的芳基氯化物与烯丙醇的交叉电子亲核反应。

Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols.

机构信息

CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.

Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China.

出版信息

Org Biomol Chem. 2021 Nov 18;19(44):9723-9731. doi: 10.1039/d1ob01874d.

DOI:10.1039/d1ob01874d
PMID:34727149
Abstract

Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols proceeds readily under mild conditions in the presence of zinc powder and MgCl to produce allylarenes in 25-92% yields. The reaction shows high regioselectivity and /-selectivity, giving linear allylation products with an configurated double bond when 1- or 3-arylallyl alcohols were used as the substrates. Functional groups including F, CF, COOEt, NMe, OMe, SiMe, OH and vinyl groups as well as nitrogen-containing heterocycles were tolerated.

摘要

镍催化芳基氯化物与烯丙醇的交叉电偶联反应在温和条件下,锌粉和 MgCl 的存在下,容易进行,以 25-92%的产率生成烯丙基芳烃。该反应具有高区域选择性和立体选择性,当 1-或 3-芳基烯丙醇作为底物时,得到具有顺式构型双键的线性烯丙基化产物。包括 F、CF、COOEt、NMe、OMe、SiMe、OH 和乙烯基基团以及含氮杂环在内的各种官能团都能兼容。

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引用本文的文献

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Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides.镍催化未活化烷基醇与芳基溴的对映收敛性脱氧还原交叉偶联反应。
Nat Commun. 2024 Mar 28;15(1):2733. doi: 10.1038/s41467-024-46713-x.
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Nickel-catalyzed arylative substitution of homoallylic alcohols.
镍催化的高烯丙醇的芳基化取代反应。
Chem Sci. 2022 Aug 12;13(39):11607-11613. doi: 10.1039/d2sc01716d. eCollection 2022 Oct 12.