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镍催化的烯烃反马氏氢芳基化反应。

Nickel-catalyzed anti-Markovnikov hydroarylation of alkenes.

作者信息

Nguyen Julia, Chong Andrea, Lalic Gojko

机构信息

Department of Chemistry , University of Washington , Seattle , Washington 98195 , USA . Email:

出版信息

Chem Sci. 2019 Feb 13;10(11):3231-3236. doi: 10.1039/c8sc05445b. eCollection 2019 Mar 21.

DOI:10.1039/c8sc05445b
PMID:30996906
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6429615/
Abstract

We have developed a nickel-catalyzed hydroarylation of alkenes using aryl halides as coupling partners. Excellent anti-Markovnikov selectivity is achieved with aryl-substituted alkenes and enol ethers. We also show that hydroarylation occurs with alkyl substituted alkenes to yield linear products. Preliminary examination of the reaction mechanism suggests irreversible hydrometallation as the selectivity determining step of the hydroarylation.

摘要

我们已经开发出一种以芳基卤化物作为偶联伙伴的镍催化烯烃氢芳基化反应。对于芳基取代的烯烃和烯醇醚,可实现优异的反马氏选择性。我们还表明,氢芳基化反应能与烷基取代的烯烃发生,生成线性产物。对反应机理的初步研究表明,不可逆的氢金属化是氢芳基化反应选择性的决定步骤。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5549/6429615/7a0672f85985/c8sc05445b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5549/6429615/630895dd2118/c8sc05445b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5549/6429615/1da6e2da7d77/c8sc05445b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5549/6429615/7a0672f85985/c8sc05445b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5549/6429615/630895dd2118/c8sc05445b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5549/6429615/1da6e2da7d77/c8sc05445b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5549/6429615/7a0672f85985/c8sc05445b-s3.jpg

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