HFIP-promoted strain-release rearrangement/N-functionalization of azabicyclo[1.1.0]butanes with para-quinone methides for the synthesis of azetidines

Haijian Wu; Manman Sun; Zhiming Wang; Jianguo Yang; Gangguo Zhu

doi:10.1039/d6cc01195k

January 1, 2026Chemical Communications

HFIP-promoted strain-release rearrangement/N-functionalization of azabicyclo[1.1.0]butanes with para-quinone methides for the synthesis of azetidines

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Key Points

The aim is to establish a metal-free method for synthesizing N-alkyl-substituted azetidines using azabicyclo[1.1.0]butanes and para-quinone methides.
Utilized a dual activation approach with HFIP for rearrangement and N-alkylation.
Focused on strain-release-driven rearrangement of ABBs with p-QMs.
Employed a metal-free and atom-economic methodology.
Successfully synthesized N-alkyl-substituted azetidines with high efficiency.
Demonstrated significant strain release contributing to the reaction's success.

Implication

Demonstrates effective N-alkylation in azetidines, implying new synthetic pathways.

Abstract

A metal-free and atom-economic methodology for N-alkyl-substituted azetidines through strain-release-driven rearrangement/N-alkylation of ABBs with p-QMs is reported, in which HFIP plays the key factor acting as a dual activator. The...

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Cite This Study

Wu et al. (2026) studied this question.

synapsesocial.com/papers/69ec5bd288ba6daa22dad1e0 https://doi.org/10.1039/d6cc01195k

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HFIP-promoted strain-release rearrangement/N-functionalization of azabicyclo[1.1.0]butanes with para-quinone methides for the synthesis of azetidines

Key Points

Implication

Abstract

Discussion

Cite This Study

HFIP-promoted strain-release rearrangement/N-functionalization of azabicyclo[1.1.0]butanes with para-quinone methides for the synthesis of azetidines

Key Points

Implication

Abstract

Discussion

Cite This Study

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