One‐pot Synthesis of Oxindoles through C−H Alkylation and Intramolecular Cyclization of Azobenzenes with Internal Olefins. Issue 14 (8th May 2017)

• Record Type: Journal Article
• Authors: Han, Sang Hoon; Mishra, Neeraj Kumar; Jo, Hyeim; Oh, Yongguk; Jeon, Mijin; Kim, Saegun; Kim, Woo Jung; Lee, Jong Suk; Kim, Hyung Sik; Kim, In Su
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 14(2017)
• Page Start: 2396
• Page End: 2401
• Publication Date: 2017-05-08
• Subjects: Azobenzenes -- C−H Activation -- Internal olefins -- Cyclization -- Oxindoles -- Rhodium; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201700147
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The rhodium(III)‐catalyzed site‐selective C−H alkylation of azobenzenes and internal olefins, such as maleimides, maleates and fumarates, followed by reductive intramolecular cyclization is described. A cationic rhodium catalyst in the presence of acetic acid additive in dichloroethane solvent was found to be the optimal catalytic system for the construction of ortho ‐alkylated azobenzenes, which smoothly underwent the intramolecular cyclization leading to the formation of C3‐functionalized oxindoles in the presence of zinc powder and acetic acid. The formed oxindole scaffold could be an important asset towards the development of novel bioactive compounds. Abstract :