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镍催化未活化烯烃的还原芳基烷基化反应。

Ni-catalysed reductive arylalkylation of unactivated alkenes.

作者信息

Jin Youxiang, Wang Chuan

机构信息

National Laboratory for Physical Science at the Microscale , Department of Chemistry , Center for Excellence in Molecular Synthesis , Hefei University of Science and Technology of China , 96 Jinzhai Road , Hefei , Anhui 20237 , P. R. China . Email:

出版信息

Chem Sci. 2018 Dec 4;10(6):1780-1785. doi: 10.1039/c8sc04279a. eCollection 2019 Feb 14.

DOI:10.1039/c8sc04279a
PMID:30842845
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6369408/
Abstract

In this protocol Ni-catalysed reductive arylalkylation of unactivated alkenes tethered to aryl bromides with primary alkyl bromides has been accomplished, providing a new path to construct diverse benzene-fused carbo- and heterocyclic cores including indanes, tetrahydroisoquinolines, indolines and isochromanes. Notably, this new method circumvents the pregeneration of organometallics and demonstrates high tolerance to a wide range of functional groups. The preliminary mechanistic investigations suggest a reaction pathway with an intermediate reduction.

摘要

在本方案中,已实现了镍催化的与芳基溴相连的未活化烯烃与伯烷基溴的还原芳基烷基化反应,为构建包括茚满、四氢异喹啉、二氢吲哚和异苯并二氢吡喃在内的多种稠合苯的碳环和杂环核心提供了一条新途径。值得注意的是,这种新方法避免了有机金属化合物的预生成,并对多种官能团表现出高耐受性。初步的机理研究表明了一条具有中间体还原的反应途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/2fd726a62a9e/c8sc04279a-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/6bf31a0b28d9/c8sc04279a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/cd4132fc3fdd/c8sc04279a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/d3f893ede7f6/c8sc04279a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/117735f3b485/c8sc04279a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/f18c435554a9/c8sc04279a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/2fd726a62a9e/c8sc04279a-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/6bf31a0b28d9/c8sc04279a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/cd4132fc3fdd/c8sc04279a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/d3f893ede7f6/c8sc04279a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/117735f3b485/c8sc04279a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/f18c435554a9/c8sc04279a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e4f/6369408/2fd726a62a9e/c8sc04279a-s6.jpg

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