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烷基双三氟甲磺酰亚胺介导的电化学脱氨基官能化反应

Alkyl bistriflimidate-mediated electrochemical deaminative functionalization.

作者信息

Shu Hui, Tao Xiangzhang, Ni Shengyang, Liu Jiyang, Xu Jia, Pan Yi, Wang Yi

机构信息

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Collaborative Innovation Center of Advanced Microstructures, School of Chemistry and Chemical Engineering, Nanjing University Nanjing 210023 China

出版信息

Chem Sci. 2024 Dec 24;16(6):2682-2689. doi: 10.1039/d4sc06773h. eCollection 2025 Feb 5.

DOI:10.1039/d4sc06773h
PMID:39802693
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11716712/
Abstract

An efficient electrochemical strategy for the deaminative functionalization of alkyl amines has been described. The alkyl bistriflimidates were readily accessed by the treatment of alkyl amines with trifluoromethanesulfonic anhydride and unprecedentedly employed for C-N bond activation. They can be applied to a range of transformations, including borylation, sulfuration, selenation, sulfonation, Additionally, deaminative esterification and amidation can be performed under catalytic base conditions. The protocol features an undivided cell without the use of transition metal- or photo-catalysts and exhibits high conversion and stability in flow reactors.

摘要

描述了一种用于烷基胺脱氨基官能化的高效电化学策略。通过用三氟甲磺酸酐处理烷基胺可轻松得到烷基双三氟甲磺酰亚胺,并前所未有的将其用于C-N键活化。它们可应用于一系列转化反应,包括硼化、硫化、硒化、磺化。此外,脱氨基酯化和酰胺化反应可在催化碱条件下进行。该方案的特点是采用无隔膜电池,无需使用过渡金属或光催化剂,并且在流动反应器中表现出高转化率和稳定性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/952db4bc0ce7/d4sc06773h-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/b379e6d33ca5/d4sc06773h-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/56be3f7596f3/d4sc06773h-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/5f31aa31b9f7/d4sc06773h-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/952db4bc0ce7/d4sc06773h-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/b379e6d33ca5/d4sc06773h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/b4b6f64d51cd/d4sc06773h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/56be3f7596f3/d4sc06773h-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/5f31aa31b9f7/d4sc06773h-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/addb/11795772/952db4bc0ce7/d4sc06773h-f5.jpg

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本文引用的文献

1
Isonitriles as Alkyl Radical Precursors in Visible Light Mediated Hydro- and Deuterodeamination Reactions.异腈作为可见光介导的氢脱氨基和氘代脱氨基反应中的烷基自由基前体
Angew Chem Int Ed Engl. 2024 Feb 12;63(7):e202317683. doi: 10.1002/anie.202317683. Epub 2024 Jan 12.
2
Enabling Al sacrificial anodes in tetrahydrofuran electrolytes for reductive electrosynthesis.在四氢呋喃电解质中实现用于还原电合成的铝牺牲阳极。
Chem Sci. 2023 Nov 2;14(45):13108-13118. doi: 10.1039/d3sc04725c. eCollection 2023 Nov 22.
3
Late-Stage Isotopic Exchange of Primary Amines.
伯胺的后期同位素交换
J Am Chem Soc. 2023 Nov 8;145(44):24367-24374. doi: 10.1021/jacs.3c09442. Epub 2023 Oct 27.
4
Electrooxidative Activation of B-B Bond in B cat : Access to gem-Diborylalkanes via Paired Electrolysis.Bcat 中 B-B 键的电氧化活化:通过成对电解获得偕二硼基烷烃。
Angew Chem Int Ed Engl. 2023 Mar 27;62(14):e202218179. doi: 10.1002/anie.202218179. Epub 2023 Feb 20.
5
Direct Deaminative Functionalization.直接脱氨官能化。
J Am Chem Soc. 2023 Jan 11;145(1):17-24. doi: 10.1021/jacs.2c11453. Epub 2022 Dec 22.
6
Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.Katritzky 盐的碎片化在形成 C-C、C-B 和 C-S 键方面的最新进展。
Top Curr Chem (Cham). 2022 May 19;380(4):25. doi: 10.1007/s41061-022-00381-x.
7
Electrochemically driven cross-electrophile coupling of alkyl halides.电化学驱动的卤代烷烃的交叉亲电偶联。
Nature. 2022 Apr;604(7905):292-297. doi: 10.1038/s41586-022-04540-4. Epub 2022 Feb 21.
8
Preparation of Primary and Secondary Dialkylmagnesiums by a Radical I/Mg-Exchange Reaction Using sBu Mg in Toluene.通过在甲苯中使用仲丁基镁进行自由基碘/镁交换反应制备伯烷基和仲烷基镁。
Angew Chem Int Ed Engl. 2022 Mar 21;61(13):e202116625. doi: 10.1002/anie.202116625. Epub 2022 Feb 9.
9
Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins.手性选择性脱氨烷基化氨基酸衍生物与非活化烯烃。
J Am Chem Soc. 2022 Jan 26;144(3):1130-1137. doi: 10.1021/jacs.1c12350. Epub 2022 Jan 14.
10
What is in Our Kit? An Analysis of Building Blocks Used in Medicinal Chemistry Parallel Libraries.我们的工具包中有哪些内容?药用化学平行文库构建模块的分析。
J Med Chem. 2021 Dec 9;64(23):17115-17122. doi: 10.1021/acs.jmedchem.1c01139. Epub 2021 Nov 22.