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钯催化炔烃的羰基碳全氟烷基化反应。通过空间 C-F 偶联反应探究氟烷基取代烯烃的构型。

Pd-Catalyzed Carbonylative Carboperfluoroalkylation of Alkynes. Through-Space C-F Coupling as a Probe for Configuration Assignment of Fluoroalkyl-Substituted Olefins.

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.

出版信息

J Org Chem. 2017 Aug 4;82(15):7998-8007. doi: 10.1021/acs.joc.7b01236. Epub 2017 Jul 20.

DOI:10.1021/acs.joc.7b01236
PMID:28677978
Abstract

A four-component Pd-catalyzed protocol for direct synthesis of perfluoroalkyl-substituted enones is reported. Under mild conditions and low catalyst loading, alkynes, iodoperfluoroalkanes, (hetero)arylboronic acids, and carbon monoxide are assembled into highly elaborate products with good yields and excellent regio- and stereoselectivities. The configuration of the products was confirmed by the observation of through-space C-F couplings, accessible through the analysis of routine C NMR spectra.

摘要

本文报道了一种四组分钯催化的直接合成全氟烷基取代烯酮的方法。在温和的条件和低催化剂负载下,炔烃、碘代全氟烷烃、(杂)芳基硼酸和一氧化碳被组装成具有良好收率和优异区域及立体选择性的高度复杂产物。通过分析常规 C NMR 谱可获得的通过空间 C-F 偶合,可确定产物的构型。

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