Intramolecular Copper(I)‐Catalyzed Interrupted Click–Acylation Domino Reaction. Issue 38 (7th August 2019)

• Record Type: Journal Article
• Authors: Larin, Egor M.; Lautens, Mark
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 38(2019)
• Page Start: 13438
• Page End: 13442
• Publication Date: 2019-08-07
• Subjects: acylation -- click chemistry -- copper catalysis -- cyclization -- domino reaction; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201907448
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Acyl substituted triazoles are valuable scaffolds, but the direct synthesis of these moieties from terminal alkynes by copper catalysis remains unexplored. We report a robust, general, and efficient method using a simple CuI/2, 2′‐bipyridine catalytic system. This transformation involves a copper catalyzed azide‐alkyne cycloaddition (CuAAC) followed by an intramolecular acylation onto a carbamoyl chloride. The reaction proceeds under mild conditions, tolerates several functional groups, and is readily scalable. This method represents a novel strategy towards the synthesis of complex heterocycles by a CuAAC/acylation domino process. Abstract : Acyl substituted triazoles were synthesized by a copper catalyzed azide alkyne cycloaddition–acylation cascade in good yields. The developed reaction provides an efficient and mild approach towards otherwise difficult‐to‐synthesize complex heterocycles.