Regioselective Synthesis of 1,2,3-Trisubstituted Pyrroles via Addition–Cyclization of Crotonate-Derived Sulfonium Salts with a Carboxylic Acid and an Amine
Abstract
High Resolution Image Download MS PowerPoint Slide A sequential addition-cyclization reaction between carboxylic acids, crotonate sulfonium salts, and amines has been developed for the construction of 1,2,3-trisubstituted pyrroles. The reaction involves regioselective addition of crotonate sulfonium salts directly to in situ -activated carboxylic acids to construct the first C–C bond, followed by cyclization with a primary amine to create the two C–N bonds in one pot. The new transformation appears to have a general substrate scope, uses readily accessible starting materials, and proceeds rapidly at room temperature. The reaction is versatile and scalable, making it suitable for applications in process and medicinal chemistry.
Fields of Study & Subjects
Synthesis and Characterization of Pyrroles
Organic Chemistry Synthesis Methods
Synthesis and Reactivity of Sulfur-Containing Compounds
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 10
- Pages
- 3776–3788
- Publication date
- 2 March 2026
- Language
- EN