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使用氟仿的气/液相微流三氟甲基化反应:醛、酮、查尔酮和亚磺酰亚胺的三氟甲基化反应

Gas/Liquid-Phase Micro-Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and -Sulfinylimines.

作者信息

Hirano Kazuki, Gondo Satoshi, Punna Nagender, Tokunaga Etsuko, Shibata Norio

机构信息

Department of Life Science and Applied Chemistry, Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 Japan.

Institute of Advanced Fluorine-Containing Materials Zhejiang Normal University 688 Yingbin Avenue 321004 Jinhua China.

出版信息

ChemistryOpen. 2019 Feb 5;8(4):406-410. doi: 10.1002/open.201800286. eCollection 2019 Apr.

DOI:10.1002/open.201800286
PMID:30976483
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6442697/
Abstract

A micro-flow nucleophilic trifluoromethylation of carbonyl compounds using gaseous fluoroform was developed. This method also allows the first micro-flow transformation of -sulfinylimines into trifluoromethyl amines with excellent diastereoselectivity. To demonstrate the synthetic utility of this micro-flow synthesis, the formal micro-flow synthesis of Efavirenz is described.

摘要

开发了一种使用气态氟仿对羰基化合物进行微流亲核三氟甲基化反应的方法。该方法还首次实现了将亚磺酰亚胺以优异的非对映选择性微流转化为三氟甲基胺。为了证明这种微流合成的实用性,本文描述了依法韦仑的形式微流合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/3fbaf7fc6594/OPEN-8-406-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/b5bf2f6a8718/OPEN-8-406-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/4f02e54a2f69/OPEN-8-406-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/ee95a842df35/OPEN-8-406-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/76cec6334b1b/OPEN-8-406-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/9ae8e0148cd6/OPEN-8-406-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/3fbaf7fc6594/OPEN-8-406-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/b5bf2f6a8718/OPEN-8-406-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/4f02e54a2f69/OPEN-8-406-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/ee95a842df35/OPEN-8-406-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/76cec6334b1b/OPEN-8-406-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/9ae8e0148cd6/OPEN-8-406-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0d2/6442697/3fbaf7fc6594/OPEN-8-406-g006.jpg

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2
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Chem Commun (Camb). 2018 Apr 24;54(34):4294-4297. doi: 10.1039/c8cc01526k.
3
Organocatalyzed Decarboxylative Trichloromethylation of Morita-Baylis-Hillman Adducts in Batch and Continuous Flow.
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