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Updated: Feb 7, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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Published on: April 10, 2015

Azetidine-Borane Complexes: Synthesis, Reactivity, and Stereoselective Functionalization.

Michael Andresini¹, Sonia De Angelis¹, Antonella Uricchio¹

¹Department of Pharmacy-Drug Sciences , University of Bari "A. Moro" , Via E. Orabona 4 , Bari 70125 , Italy.

The Journal of Organic Chemistry

|July 20, 2018

Summary

This study introduces azetidine-borane complexes, detailing their synthesis and reactivity in lithiation. Temperature-controlled reactions enable stereoselective synthesis, with a syn configuration crucial for regioselective lithiation at the benzylic position.

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Area of Science:

Organic Chemistry
Organometallic Chemistry

Background:

Azetidines are strained four-membered nitrogen-containing heterocycles with diverse applications.
Borane complexes are valuable reagents in organic synthesis.
Understanding the reactivity of azetidine-borane complexes is key to developing new synthetic methodologies.

Purpose of the Study:

To report the synthesis and structural characterization of novel azetidine-borane complexes.
To investigate the reactivity of these complexes in lithiation reactions.
To explore the stereoselectivity and regioselectivity of these transformations.

Main Methods:

Synthesis of azetidine-borane complexes via reaction of borane with N-alkyl-2-arylazetidines.
Temperature-dependent stereoselective synthesis.
Lithiation reactions and investigation of regioselectivity.
Computational studies to support experimental findings.

Main Results:

Successful synthesis and structural determination of azetidine-borane complexes.
Demonstration of temperature-dependent stereoselectivity in complex formation.
Observation of regioselective hydrogen/lithium permutation at the benzylic position in lithiation reactions.
Identification of a syn relationship between ring proton and BH3 group as critical for reactivity.
Development of a new synthetic strategy for N-alkyl-2,2-disubstituted azetidines.

Conclusions:

Azetidine-borane complexes exhibit unique reactivity in lithiation reactions.
Stereochemical control is crucial for achieving regioselective functionalization.
The BH3 group likely facilitates lithiation through an electrostatic complex induced proximity effect.
This work provides new synthetic routes to valuable azetidine derivatives.