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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.

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/b379e6d33ca5/d4sc06773h-f1.jpg

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