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Alkyl bistriflimidate-mediated electrochemical deaminative functionalization.

Hui Shu1, Xiangzhang Tao1, Shengyang Ni1

  • 1State 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 yiwang@nju.edu.cn taoxz941006@163.com.

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This study introduces an electrochemical method for deaminative functionalization of alkyl amines using alkyl bistriflimidates. This novel approach enables C-N bond activation for various transformations without metal catalysts.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • Alkyl amines are versatile building blocks in organic synthesis.
  • Efficient methods for C-N bond activation are crucial for synthesizing complex molecules.
  • Existing deaminative functionalization strategies often require harsh conditions or expensive catalysts.

Purpose of the Study:

  • To develop an efficient electrochemical strategy for the deaminative functionalization of alkyl amines.
  • To explore the use of alkyl bistriflimidates as key intermediates for C-N bond activation.
  • To establish a versatile and sustainable protocol applicable to various transformations.

Main Methods:

  • Electrochemical synthesis using an undivided cell.
  • Preparation of alkyl bistriflimidates from alkyl amines and trifluoromethanesulfonic anhydride.
  • Application in borylation, sulfuration, selenation, sulfonation, esterification, and amidation reactions.

Main Results:

  • Successful deaminative functionalization of alkyl amines was achieved.
  • Alkyl bistriflimidates were effectively used for C-N bond activation.
  • The protocol demonstrated high conversion and stability in flow reactors.
  • Metal- and photo-catalyst-free conditions were employed.

Conclusions:

  • A novel and efficient electrochemical strategy for alkyl amine functionalization has been established.
  • The developed method offers a sustainable and versatile route for C-N bond activation.
  • The protocol's applicability in flow chemistry highlights its potential for scalability.