Work

Triiodide‐Mediated δ‐Amination of Secondary C−H Bonds

Year: 2016

Type: article

Abstract: The Cδ -H amination of unactivated, secondary C-H bonds to form a broad range of functionalized pyrrolidines has been developed by a triiodide (I3 (-) )-mediated strategy. By in situ 1) oxidation of sodium iodide and 2) sequestration of the transiently generated iodine (I2 ) as I3 (-) , this approach precludes undesired I2 -mediated decomposition which can otherwise limit synthetic utility to only weak C(sp(3) )-H bonds. The mechanism of this triiodide-mediated cyclization of unbiased, secondary C(sp(3) )-H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201604704

Authors: Ethan A. Wappes, Stacy C. Fosu, Trevor C. Chopko, David A. Nagib

Institution: The Ohio State University

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: Chemistry/Biology Interface Training Grant, Radical Chaperones to Harness Remote, Selective C-H Functionalization Mechanisms