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Updated: Jul 20, 2025
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
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An Acid-Controlled Method for the Regioselective Functionalization of Anilines over Aliphatic Amines
Bowen Li1, Yulun Hu1, Gregory P Tochtrop1
1Department of Chemistry, Case Western Reserve University Millis Hall 410, 2080 Adelbert Road, Cleveland, Ohio, 44106, USA.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 1, 2023
Summary
This study introduces a regioselective method for functionalizing anilines before aliphatic amines. This approach simplifies organic synthesis by avoiding protection/deprotection steps, enhancing pathway efficiency.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Regioselective transformations are crucial in organic synthesis.
- Traditional methods often involve complex protection/deprotection steps.
- Modern synthesis aims for efficiency and protecting-group-free strategies.
Purpose of the Study:
- To develop a regioselective method for functionalizing anilines over aliphatic amines.
- To exploit inherent reactivity differences between anilines and aliphatic amines.
- To establish a protecting-group-free synthetic route.
Main Methods:
- Utilized classic Baeyer-Mills reaction conditions.
- Investigated the preferential reaction of anilines in the presence of aliphatic amines.
- Extended the observed reactivity principle to other electrophiles and conditions.
Main Results:
- Anilines demonstrated preferential reactivity over aliphatic amines under Baeyer-Mills conditions.
- The regioselectivity was successfully applied to various electrophiles.
- A protecting-group-free method for aniline functionalization was established.
Conclusions:
- A novel regioselective functionalization method for anilines has been developed.
- This method offers improved efficiency in organic synthesis.
- The findings pave the way for more streamlined synthetic strategies.
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