78019-66-6Relevant academic research and scientific papers
Site-selective aliphatic C-H bromination using N -bromoamides and visible light
Schmidt, Valerie A.,Quinn, Ryan K.,Brusoe, Andrew T.,Alexanian, Erik J.
supporting information, p. 14389 - 14392 (2014/12/10)
Transformations that selectively functionalize aliphatic C-H bonds hold significant promise to streamline complex molecule synthesis. Despite the potential for site-selective C-H functionalization, few intermolecular processes of preparative value exist. Herein, we report an approach to unactivated, aliphatic C-H bromination using readily available N-bromoamide reagents and visible light. These halogenations proceed in useful chemical yields, with substrate as the limiting reagent. The site selectivities of these radical-mediated C-H functionalizations are comparable (or superior) to the most selective intermolecular C-H functionalizations known. With the broad utility of alkyl bromides as synthetic intermediates, this convenient approach will find general use in chemical synthesis.
New free-radical halogenations of alkanes, catalysed by N-hydroxyphthalimide. Polar and enthalpic effects on the chemo- and regioselectivity
Minisci, Francesco,Porta, Ombretta,Recupero, Francesco,Gambarotti, Cristian,Paganelli, Roberto,Pedulli, Gian Franco,Fontana, Francesca
, p. 1607 - 1609 (2007/10/03)
Reactions of alkanes with different halogenating systems are compared in order to explore the reactivity of phthalimido-N-oxyl radical in hydrogen abstraction; the importance of polar effects is emphasised.
