What question did this study set out to answer?

This research focuses on developing efficient methods for synthesizing imines from carbonyl compounds and isocyanates.

May 3, 2026

Al/P Frustrated Lewis pair catalyzed metathesis of carbon-heteroatom double bonds between aldehydes and isocyanates

HOHirotaka OkamotoOsaka Gakuin University YNYoshihiro NishimotoOsaka Gakuin University MYMakoto YasudaOsaka Gakuin University

Key Points

This research focuses on developing efficient methods for synthesizing imines from carbonyl compounds and isocyanates.
Utilized an Al/P frustrated Lewis pair (FLP) for catalyzing the C=O/C=N metathesis.
Investigated the mechanism revealing the role of the non-coordinating PCy2 group in catalyst regeneration.
Analyzed the reaction with aldehydes and isocyanates as substrates.
Successfully synthesized imines from aldehydes and isocyanates through FLP-catalyzed metathesis.
Revealed that the catalyst allows for effective regeneration from resting state due to reversible adduct dissociation.

Abstract

Abstract Imines are fundamental building blocks in organic synthesis, and the development of efficient methods for their preparation remains an important challenge. Metathesis between the carbon–oxygen double bond (C=O) of carbonyl compounds and the carbon–nitrogen double bond (C=N) of isocyanates offers a promising route to imines. Herein, we report an Al/P FLP-catalyzed C=O/C=N metathesis that enables the synthesis of imines from aldehydes and isocyanates. Mechanistic investigations revealed that the unique catalytic activity of an Al/P FLP bearing two PCy2 groups arises from the presence of a non-coordinating PCy2 group, which facilitates catalyst regeneration from a resting state through reversible dissociation of the aldehyde adduct.

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