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A Traceless Heterocyclic Amine Mediator in Regioselectivity-Switchable Formal [1 + 2 + 2] Cycloaddition Reaction to 1,3,4- and 1,4,5-Trisubstituted Pyrazoles.

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Switchable multicomponent reactions have been attractive tools for the construction of compound libraries with skeleton diversity and complexity by slightly changing the reaction conditions. Described herein is a regioselectivity-switchable formal… Click to show full abstract

Switchable multicomponent reactions have been attractive tools for the construction of compound libraries with skeleton diversity and complexity by slightly changing the reaction conditions. Described herein is a regioselectivity-switchable formal [1 + 2 + 2] cycloaddition reaction from difluoroalkyl compounds, enaminones, and RNHNH2, ultimately using 1-methylindazol-3-amine as a traceless mediator to switch the inherent regioselectivity of 1,3,4-trisubstituted pyrazole formation to 1,4,5-trisubstituted pyrazoles. Remarkable features of this work include mild conditions, simple operation, and broad scopes.

Keywords: reaction; regioselectivity; switchable formal; regioselectivity switchable; formal cycloaddition; cycloaddition reaction

Journal Title: Organic letters
Year Published: 2023

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