834-72-0Relevant academic research and scientific papers
Copper-Catalyzed Amide Radical-Directed Cyanation of Unactivated Csp3-H Bonds
Zhang, Hongwei,Zhou, Yulu,Tian, Peiyuan,Jiang, Cuiyu
supporting information, (2019/03/19)
A method for site-selective intermolecular δ/?-Csp3-H cyanation of aliphatic sulfonamides is developed using TsCN as the cyanating reagent, catalyzed by a Cu(I)/phenanthroline complex. The mild, expeditious, and modular protocol allows efficient remote Csp3-H cyanation with good functional group tolerance and high regioselectivity. Mechanistic studies indicate that the reaction might proceed through a Cu(I)-mediated N-F bond cleavage to generate an amidyl radical, 1,5-HAT, and cyano group transfer of the resulting carbon radical with TsCN.
Triiodide-Mediated δ-Amination of Secondary C?H Bonds
Wappes, Ethan A.,Fosu, Stacy C.,Chopko, Trevor C.,Nagib, David A.
, p. 9974 - 9978 (2016/08/16)
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(sp3)?H bonds. The mechanism of this triiodide-mediated cyclization of unbiased, secondary C(sp3)?H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.
