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钌(II)催化1,3 - 二酮与氧化锍叶立德的化学选择性脱酰基环化反应——C-C键活化

Ruthenium(ii)-catalyzed chemoselective deacylative annulation of 1,3-diones with sulfoxonium ylides C-C bond activation.

作者信息

Wen Si, Lv Weiwei, Ba Dan, Liu Jing, Cheng Guolin

机构信息

College of Materials Science & Engineering , Huaqiao University , Xiamen 361021 , China . Email:

出版信息

Chem Sci. 2019 Aug 12;10(39):9104-9108. doi: 10.1039/c9sc03245b. eCollection 2019 Oct 21.

DOI:10.1039/c9sc03245b
PMID:31827753
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6889838/
Abstract

The first successful example of deacylative annulation of 1,3-diones with sulfoxonium ylides was achieved through Ru(ii)-catalyzed C-C bond activation. The excellent chemoselectivity and broad substrate scope render this method a practical and versatile approach for the preparation of (hetero)aryl and alkenyl substituted furans, which are valuable units in many biologically active compounds and functional materials. A preliminary mechanistic study reveals that this process involves a deacylative α-ruthenation to generate key alkyl Ru(ii) intermediates with the release of a benzoic acid fragment.

摘要

通过钌(II)催化的C-C键活化实现了1,3 - 二酮与氧化锍叶立德的脱酰基环化反应的首个成功实例。出色的化学选择性和广泛的底物范围使该方法成为制备(杂)芳基和烯基取代呋喃的实用且通用的方法,这些呋喃是许多生物活性化合物和功能材料中有价值的单元。初步机理研究表明,该过程涉及脱酰基α-钌化反应,以生成关键的烷基钌(II)中间体并释放苯甲酸片段。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e52/6889838/00187f240585/c9sc03245b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e52/6889838/9a01966c5673/c9sc03245b-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e52/6889838/249be51ce99f/c9sc03245b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e52/6889838/00187f240585/c9sc03245b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e52/6889838/9a01966c5673/c9sc03245b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e52/6889838/75654f0357a2/c9sc03245b-s2.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e52/6889838/00187f240585/c9sc03245b-s5.jpg

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