Installation of α-ketocarboxylate groups to C7-position of indolines via C−H addition and oxidation approach under ruthenium catalysis. Issue 13 (30th March 2017)

• Record Type: Journal Article
• Authors: Jo, Hyeim; Park, Jihye; Mishra, Neeraj Kumar; Jeon, Mijin; Sharma, Satyasheel; Oh, Hyunjung; Lee, Seok-Yong; Jung, Young Hoon; Kim, In Su
• Is Part Of: Tetrahedron. Volume 73:Issue 13(2017)
• Page Start: 1725
• Page End: 1732
• Publication Date: 2017-03-30
• Subjects: C–H activation -- Ethyl glyoxalate -- Indolines -- Ketoesters -- Ruthenium; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.02.022
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The ruthenium(II)-catalyzed site-selective acylation of indolinic C−H bonds with ethyl glyoxalate is described. A cationic ruthenium catalyst in the presence of copper(II) acetate was found to be an optimal catalytic system for the construction of C7-indolinyl ketoesters. In this process, C−H addition reaction first takes place, and subsequent oxidation of alcohol intermediates occur in-situ. The formed C7−functionalized indolines can be a crucial array towards the construction of novel bioactive molecules. Graphical abstract: