Rh(III)‐Catalyzed [3+2] Annulation and C−H Alkenylation of Indoles with 1, 3‐Diynes by C−H Activation. Issue 15 (21st April 2021)

• Record Type: Journal Article
• Authors: Kumar, Sanjeev; Nunewar, Saiprasad; Usama, Khan Mohammad; Kanchupalli, Vinaykumar
• Is Part Of: European journal of organic chemistry. Issue 15(2021)
• Page Start: 2223
• Page End: 2229
• Publication Date: 2021-04-21
• Subjects: [3+2] annulation -- C2-alkenylations -- C−H functionalization -- Heterocycles -- Rh(III) catalyst; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100212
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Described herein is the Rh(III)‐ catalyzed [3+2] annulations and C2‐alkenylations of indoles with 1, 3‐diynes, which deliver the synthetically important 3 H ‐pyrrolo[1, 2‐ a ]indol‐3‐ones and highly functionalized tetrasubstituted olefin derivatives. Importantly, in this methodology, the additive controlled selective formation of desired scaffolds. This synthetic strategy exhibits high efficiency and broad functional group compatibility. Furthermore, this protocol has been successfully extended to the synthesis of bis‐annulated and trisubstituted alkenes. The method is also smoothly applied for the synthesis of the core structure of protein kinase C inhibitor and melatonin analogues. Abstract : In this protocol, an additive controlled Rh(III)‐catalyzed divergent synthesis of 3 H ‐pyrrolo[1, 2‐ a ]indol‐3‐ones and highly functionalized tetrasubstituted olefin derivatives is described. This synthetic strategy exhibits high efficiency and broad functional group compatibility.