[1+1+1] Cyclotrimerization for the Synthesis of Cyclopropanes. Issue 17 (21st March 2016)

• Record Type: Journal Article
• Authors: Manna, Srimanta; Antonchick, Andrey P.
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 17(2016)
• Page Start: 5290
• Page End: 5293
• Publication Date: 2016-03-21
• Subjects: copper -- cyclopropanes -- cyclotrimerization -- oxidative coupling -- radicals; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201600807
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The synthesis of small rings by functionalization of C(sp 3 )−H bonds remains a great challenge. We report for the first time a copper‐catalyzed [1+1+1] cyclotrimerization of acetophenone derivatives under mild reaction conditions. The reaction has a broad scope for the stereoselective synthesis of cyclopropanes by trimerization of acetophenone. The developed transformation is based on an extraordinary copper‐catalyzed cascade process that allows saturated carbocycles to be obtained for the first time by cyclotrimerization through functionalization of C(sp 3 )−H bonds. The cascade of sixfold C(sp 3 )−H bond functionalization allows the synthesis of cyclopropanes in a highly stereoselective approach. Abstract : Give it a tri : Copper‐catalyzed oxidative [1+1+1] cyclotrimerization of acetophenone derivatives under mild reaction conditions and with a broad reaction scope has been developed. This transformation is a radical cascade process that allows saturated carbocycles to be obtained by cyclotrimerization through functionalization of C(sp 3 )−H bonds.