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无过渡金属条件下乙烯基-1,2,3-三唑衍生物的合成

Synthesis of vinyl-1,2,3-triazole derivatives under transition metal-free conditions.

作者信息

Cui Menghan, Su Changhui, Wang Rong, Yang Qing, Kuang Chunxiang

机构信息

Shanghai Key Lab of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University Shanghai 200092 China

School of Chemistry and Life Science, Nanjing University, Jinling College Nanjing 210089 China.

出版信息

RSC Adv. 2021 Dec 6;11(61):38933-38937. doi: 10.1039/d1ra08322h. eCollection 2021 Nov 29.

DOI:10.1039/d1ra08322h
PMID:35493263
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9044274/
Abstract

Herein, we describe a novel and green route for the direct synthesis of vinyl triazole derivatives with alkynes and triazoles promoted by an inorganic base under transition metal-free conditions. The base shows great catalytic activity for the anti-Markovnikov stereoselective hydroamination of alkynes. Moreover, good yields with excellent functional group tolerance are successfully achieved for a range of substrates, including aryl and heteroaryl groups, terminal alkynes and internal alkynes, and various triazole derivatives. This work presents an advanced concept for the synthesis of alkenyl triazole with a versatile and cost-efficient approach.

摘要

在此,我们描述了一种新颖的绿色路线,用于在无过渡金属条件下,由无机碱促进炔烃和三唑直接合成乙烯基三唑衍生物。该碱对炔烃的反马氏立体选择性氢胺化反应显示出很高的催化活性。此外,对于一系列底物,包括芳基和杂芳基、末端炔烃和内炔烃以及各种三唑衍生物,都成功实现了具有优异官能团耐受性的高产率。这项工作提出了一种通用且经济高效的方法来合成烯基三唑的先进概念。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/11400a3e518b/d1ra08322h-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/29af28752dfc/d1ra08322h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/0d97c8336192/d1ra08322h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/430313476596/d1ra08322h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/168b3e411f95/d1ra08322h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/f5d1fa76f97a/d1ra08322h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/11400a3e518b/d1ra08322h-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/29af28752dfc/d1ra08322h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/0d97c8336192/d1ra08322h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/430313476596/d1ra08322h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/168b3e411f95/d1ra08322h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/f5d1fa76f97a/d1ra08322h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2bf/9044274/11400a3e518b/d1ra08322h-s5.jpg

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本文引用的文献

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