Cobalt catalyzed sp3 C–H amination utilizing aryl azides

• Type of Material: Article
• Authors: Omar Villanueva, Emory University; Nina Mace Weldy, Emory University; Simon Blakey, Emory University; Cora E. MacBeth, Emory University
• Language: English
• Date: 2015-01-01
• Publisher: Royal Society of Chemistry: Open Access
• Publication Version: Final Published Version
• Copyright Statement: © 2015 The Royal Society of Chemistry.
• License: Creative Commons Attribution 3.0 Unported
• Final Published Version (URL): http://dx.doi.org/10.1039/c5sc01162k
• Title of Journal or Parent Work: Chemical Science
• ISSN: 2041-6520
• Volume: 6
• Issue: 11
• Start Page: 6672
• End Page: 6675
• Grant/Funding Information: This research was supported by the National Science Foundation under the Center for Chemical Innovation in Selective C–H Functionalization (CHE-1205646).
• Research Categories: Geology; Engineering, Chemical

Abstract

A dinuclear Co(ii) complex supported by a modular, tunable redox-active ligand system is capable of selective C-H amination to form indolines from aryl azides in good yields at low (1 mol%) catalyst loading. The reaction is tolerant of medicinally relevant heterocycles, such as pyridine and indole, and can be used to form 5-, 6-, and 7-membered rings. The synthetic versatility obtained using low loadings of an earth abundant transition metal complex represents a significant advance in catalytic C-H amination technology.