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pH 调控的铱催化水相中烯丙基醇的 N-烯丙基化或 N-烷基化胺选择性合成。

pH-Mediated Selective Synthesis of N-Allylic Alkylation or N-Alkylation Amines with Allylic Alcohols via an Iridium Catalyst in Water.

机构信息

School of Pharmaceutical Sciences, Gannan Medical University, Ganzhou 341000, Jiangxi, P. R. China.

出版信息

J Org Chem. 2021 Nov 5;86(21):15509-15521. doi: 10.1021/acs.joc.1c01930. Epub 2021 Oct 13.

Abstract

Amination of allylic alcohols is an effective approach in the facile synthesis of -allylic alkylation or -alkylation amines. Recently, a series of catalysts were devised to push forward this transformation. However, current synthetic methods are typically limited to achieve either -allylic alkylation or -alkylation products via a certain catalyst. In this article, a pH-mediated selective synthesis of -allylic alkylation or -alkylation amines with allylic alcohols via an iridium catalyst with water as the environmental benign solvent is revealed, enabling the miscellaneous synthesis of -allylic alkylation and -alkylation products in outstanding yields. Furthermore, a gram-scale experiment with low catalyst loading offers the potential to access a distinct entry for the synthesis of the antifungal drug naftifine.

摘要

烯丙醇的胺化是一种有效方法,可以简便地合成β-烯丙基烷基化或β-烷基化胺。最近,人们设计了一系列催化剂来推动这一转化。然而,目前的合成方法通常仅限于通过特定的催化剂来实现β-烯丙基烷基化或β-烷基化产物。在本文中,我们揭示了一种通过铱催化剂在水这种环境友好的溶剂中,利用 pH 介导的选择性合成β-烯丙基烷基化或β-烷基化胺的方法,使各种β-烯丙基烷基化和β-烷基化产物以优异的收率得到合成。此外,低催化剂负载量的克级实验为合成抗真菌药物萘替芬提供了一个独特的途径。

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