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铜（II）催化烯丙醇的三组分芳基化/氢胺化串联反应：合成1-芳基-2-磺酰氨基丙烷

Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes.

作者信息

Loro Camilla, Papis Marta, Foschi Francesca, Broggini Gianluigi, Poli Giovanni, Oble Julie

机构信息

Dipartimento di Scienza e Alta Tecnologia, Università dell'Insubria, via Valleggio 11, 22100 Como, Italy.

Faculté des Sciences et Ingénierie, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, Sorbonne Université, 4 place Jussieu, 75005 Paris, France.

出版信息

J Org Chem. 2023 Oct 6;88(19):13995-14003. doi: 10.1021/acs.joc.3c01536. Epub 2023 Sep 25.

DOI:10.1021/acs.joc.3c01536
PMID:37747795
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10563128/
Abstract

A new straightforward approach to 1-aryl-2-aminopropanes using easily accessible substrates has been developed. Simple allyl alcohol is shown to be an ideal synthetic equivalent of the C3 propane-1,2-diylium bis-cation synthon in three-component cascade reactions with arenes and sulfonamide nucleophiles to regioselectively afford 1-aryl-2-aminopropanes. The reaction is catalyzed by Cu(OTf) and is expected to involve a Friedel-Crafts-type allylation of the arene, followed by hydroamination.

摘要

一种使用易于获得的底物合成1-芳基-2-氨基丙烷的新的直接方法已经被开发出来。在与芳烃和磺酰胺亲核试剂的三组分串联反应中，简单的烯丙醇被证明是C3丙烷-1,2-二亚胺双阳离子合成子的理想合成等效物，能够区域选择性地得到1-芳基-2-氨基丙烷。该反应由Cu(OTf)催化，预计涉及芳烃的傅克型烯丙基化反应，随后是氢胺化反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a271/10563128/6890eaadd981/jo3c01536_0008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a271/10563128/6890eaadd981/jo3c01536_0008.jpg

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