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镍催化芳基炔基酸与四烷基二硫化秋兰姆的酰胺化反应：芳基炔基酰胺的简便合成方法

Nickel-Catalyzed Amidation of Aryl Alkynyl Acids with Tetraalkylthiuram Disulfides: A Facile Synthesis of Aryl Alkynyl Amides.

作者信息

Wang Longfei, Qiu Jianhua, Zhang Bohai, Chen Mengqi, Wang Hongxia, Miao Xiaohui, Wu Zhiyong, Zhao Mingqin, Shen Hongtao, Lai Miao, Shi Xiangdong

机构信息

Flavors and Fragrance Engineering & Technology Research Center of Henan Province, College of Tobacco Science, Henan Agricultural University, Zhengzhou 450002, P. R. China.

Technology Center, China Tobacco Henan Industrial Co., Ltd., Zhengzhou 450000, Henan, China.

出版信息

ACS Omega. 2023 Feb 15;8(8):7699-7713. doi: 10.1021/acsomega.2c07353. eCollection 2023 Feb 28.

DOI:10.1021/acsomega.2c07353
PMID:36872968
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9979367/
Abstract

Nickel-catalyzed amidation of aryl alkynyl acids using tetraalkylthiuram disulfides as the amine source is described, affording a series of aryl alkynyl amides in good to excellent yields under mild conditions. This general methodology provides an alternative pathway for the synthesis of useful aryl alkynyl amides in an operationally simple manner, which shows its practical synthetic value in organic synthesis. The mechanism of this transformation was explored through control experiments and DFT calculations.

摘要

本文描述了使用四烷基二硫化秋兰姆作为胺源，通过镍催化芳基炔酸的酰胺化反应，在温和条件下以良好至优异的产率得到一系列芳基炔酰胺。这种通用方法以操作简单的方式为有用的芳基炔酰胺的合成提供了一条替代途径，在有机合成中显示出其实际的合成价值。通过对照实验和密度泛函理论（DFT）计算探索了这种转化的机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/22d296063562/ao2c07353_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/81cd5aaeb44e/ao2c07353_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/0df843093236/ao2c07353_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/59807cc2ed2a/ao2c07353_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/6288f4f38b75/ao2c07353_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/10bfc40ef226/ao2c07353_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/22d296063562/ao2c07353_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/81cd5aaeb44e/ao2c07353_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/0df843093236/ao2c07353_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/59807cc2ed2a/ao2c07353_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/6288f4f38b75/ao2c07353_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/10bfc40ef226/ao2c07353_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/497b/9979367/22d296063562/ao2c07353_0007.jpg

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Org Lett. 2019 Sep 20;21(18):7484-7488. doi: 10.1021/acs.orglett.9b02784. Epub 2019 Sep 9.
3
Regioselective Synthesis of Sulfonyl-Containing Benzyl Dithiocarbamates through Copper-Catalyzed Thiosulfonylation of Styrenes.
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J Org Chem. 2019 Sep 6;84(17):11135-11149. doi: 10.1021/acs.joc.9b01829. Epub 2019 Aug 23.
4
Metal-Free Transfer Hydroiodination of C-C Multiple Bonds.无金属转移氢碘酸化 C-C 多重键。
J Am Chem Soc. 2019 Jan 16;141(2):1135-1140. doi: 10.1021/jacs.8b12318. Epub 2018 Dec 28.
5
SOF-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes.索非布韦介导的醇类氧化脱氢和脱水转化为炔烃
J Am Chem Soc. 2018 Dec 19;140(50):17666-17673. doi: 10.1021/jacs.8b10069. Epub 2018 Dec 11.
6
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Angew Chem Int Ed Engl. 2012 Mar 26;51(13):3231-5. doi: 10.1002/anie.201108763. Epub 2012 Feb 15.