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镍催化外消旋炔丙基卤化物与芳基锌试剂的不对称交叉偶联反应。

Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagents.

作者信息

Smith Sean W, Fu Gregory C

机构信息

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

出版信息

J Am Chem Soc. 2008 Sep 24;130(38):12645-7. doi: 10.1021/ja805165y. Epub 2008 Sep 3.

DOI:10.1021/ja805165y
PMID:18763769
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2626171/
Abstract

A stereoconvergent method for the catalytic asymmetric Negishi cross-coupling of racemic secondary propargylic halides with arylzinc reagents has been developed. Neither family of compounds has previously been shown to be a suitable partner in such coupling processes. From a practical point of view, it is noteworthy that the catalyst components (NiCl2.glyme and pybox ligand 1) are commercially available.

摘要

已开发出一种立体收敛方法,用于外消旋仲炔丙基卤化物与芳基锌试剂的催化不对称Negishi交叉偶联反应。此前尚未证明这两类化合物在此类偶联反应中是合适的反应伙伴。从实际角度来看,值得注意的是催化剂组分(NiCl2·甘醇二甲醚和吡唑啉酮配体1)可从商业渠道购得。

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J Org Chem. 2008 May 16;73(10):3680-8. doi: 10.1021/jo702497p. Epub 2008 Apr 15.
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Chem Rev. 2023 Oct 25;123(20):11817-11893. doi: 10.1021/acs.chemrev.3c00059. Epub 2023 Oct 4.
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J Am Chem Soc. 2008 Mar 19;130(11):3302-3. doi: 10.1021/ja8009428. Epub 2008 Feb 27.
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