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通过镍五羧基环戊二烯基二酰胺催化的末端环氧化物硅氢化反应制备伯醇。

Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides.

作者信息

Steiniger Keri A, Lambert Tristan H

机构信息

Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.

出版信息

Org Lett. 2021 Oct 15;23(20):8013-8017. doi: 10.1021/acs.orglett.1c03029. Epub 2021 Oct 6.

Abstract

The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.

摘要

报道了一种由五羧基环戊二烯基(PCCP)二酰胺镍配合物和路易斯酸共同催化的环氧化物高效区域选择性硅氢化反应。该方法可实现末端单取代环氧化物的还原开环,生成无支链的伯醇。一系列底物(包括末端和非末端环氧化物)均显示有效,并提供了机理依据。这项工作代表了首次使用PCCP衍生物作为过渡金属催化的配体。

相似文献

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Regioselective hydrosilylation of epoxides catalysed by nickel(ii) hydrido complexes.
Chem Commun (Camb). 2017 Apr 13;53(31):4308-4311. doi: 10.1039/c7cc01655g.

本文引用的文献

8
Methods for the Synthesis of Functionalized Pentacarboxycyclopentadienes.功能化五羧基环戊二烯的合成方法。
Org Lett. 2017 Aug 18;19(16):4227-4230. doi: 10.1021/acs.orglett.7b01867. Epub 2017 Aug 3.
9
Regioselective hydrosilylation of epoxides catalysed by nickel(ii) hydrido complexes.
Chem Commun (Camb). 2017 Apr 13;53(31):4308-4311. doi: 10.1039/c7cc01655g.

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