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Updated: Jul 11, 2026

A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor
Published on: February 10, 2023
An efficient and mild bismuth triflate-catalysed three-component Mannich-type reaction.
Thierry Ollevier1, Etienne Nadeau
1Département de Chimie, Université Laval, Québec, Canada. thierry.ollevier@chm.ulaval.ca
A new catalytic method enables aldehydes and amines to react with silyl enolates, forming Mannich-type adducts. This efficient synthesis yields beta-amino ketones and esters in high amounts.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Mannich reactions are fundamental in organic synthesis for C-C bond formation.
- Silyl enolates are versatile nucleophiles in organic transformations.
- Development of efficient catalytic systems for Mannich-type reactions is ongoing.
Purpose of the Study:
- To develop a novel catalytic system for the synthesis of Mannich-type adducts.
- To explore the reactivity of various silyl enolates in the presence of aldehydes and amines.
- To achieve high yields and efficiency in the formation of beta-amino ketones and esters.
Main Methods:
- Utilizing bismuth triflate tetrahydrate (Bi(OTf)(3).4H(2)O) as a catalyst.
- Reacting aldehydes with amines and silyl enolates.
- Employing silyl enolates derived from ketones, esters, and thioesters.
Main Results:
- Aldehydes, amines, and silyl enolates react smoothly under catalytic conditions.
- A wide range of silyl enolates efficiently form Mannich-type adducts.
- High yields (up to 94%) of beta-amino ketones and beta-amino esters were obtained.
Conclusions:
- The developed catalytic system provides an efficient route to Mannich-type adducts.
- Bismuth triflate is an effective catalyst for this transformation.
- The method offers a valuable tool for synthesizing beta-amino carbonyl compounds.
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