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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

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Oxygen atom transfer: a mild and efficient method for generating iminyl radicals.

Youngsuk Kim¹, Christopher W Bielawski², Eunsung Lee³

¹Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673, Republic of Korea. eslee@postech.ac.kr and Center for Self-assembly and Complexity (CSC), Institute for Basic Science (IBS), Pohang, 37673, Republic of Korea.

Chemical Communications (Cambridge, England)

|May 31, 2019

Summary

Oxygen atom transfer reactions convert iminoxyl species into iminyl radicals. Computational studies reveal key intermediates and N-O bond cleavage leading to radical formation localized on nitrogen atoms.

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Area of Science:

Organic Chemistry
Computational Chemistry

Background:

Iminoxyl species are important radical intermediates.
Understanding their reactivity is crucial for synthetic applications.

Purpose of the Study:

To elucidate the mechanism of oxygen atom transfer from acceptors to iminoxyl species.
To characterize the intermediates and products of this reaction.

Main Methods:

Density Functional Theory (DFT) calculations.
Analysis of reaction pathways and intermediate structures.
Spin density distribution analysis.

Main Results:

Oxygen atom transfer from acceptors like triphenylphosphine (PPh3) to iminoxyl species was confirmed.
Key intermediates formed through association between reactants were identified.
Homolytic cleavage of the N-O bond in intermediates generates iminyl radicals.
Spin density in the resulting iminyl radicals is localized on exocyclic nitrogen atoms.

Conclusions:

The reaction proceeds via association and subsequent N-O bond cleavage.
This mechanism provides a route to synthetically useful iminyl radicals.