Selectfluor-mediated intermolecular C–O cross coupling reaction for the synthesis of N-hydroxyimide esters was achieved under metal-free conditions.

In this study, visible‐light‐induced [3+2] cyclization reactions of hydrazones with hypervalent iodine diazo reagents as diazomethyl radical precursors are reported. Mild reaction conditions, a broad substrate scope, and excellent functional group compatibility were observed. Furthermore, the synthetic utility was demonstrated by gram‐scale synthesis and elaboration to several value‐added products. This protocol broadens the scope of diazo chemistry, and is applicable to the late‐stage functionalization of natural products.

In this study, a radical-triggered cyclization of o-alkenyl aromatic isocyanides prepared from accessible starting materials is developed. The reaction provides a general and efficient method for the synthesis of 4-CN-2-CF 3 /CF 2 H-containing quinolines under copper or visible-light photoredox catalysis in a one-pot synthetic procedure. This protocol demonstrates good to high yields, broad substrate scope, and good functional group tolerance.

A practical, simple, and efficient copper-catalyzed highly regioselective oxyalkylation of styrenes and readily available a-bromoacetamides under air is realized. This reaction exhibits a wide range of functional group tolerance in styrenes and a-bromoacetamides to afford iminolactones.Difunctionalization of alkenes is a powerful tool for the synthesis of heterocycles through tandem two same or different C-X (X ¼ C, N, O, etc.) bond formations in organic synthesis. Although metal-free as well as transition-metalcatalyzed aminocarbonylation, aminoarylation, aminovinylation, aminoalkynylation, and aminooxygenation reactions of alkenes have been signicant developments in recent decades, 1 the selective oxyalkylation reactions of alkenes for their efficiency in synthesizing different types of oxygencontaining heterocycles remains challenging.2 N-Substituted iminolactones, which can be easily converted to g-lactones, are prevalently used as antibacterial agents, aldosterone inhibitors, and proper precursors for the preparation of a wide spectrum of natural compounds.3 However, the selective oxyalkylation of alkenes for the synthesis of N-substituted iminolactones are still rare. In this context, Lei and coworkers developed Ni-catalyzed cyclization of a-haloamides with alkenes through carbon-centered radical addition to the carbonyl oxygen of amides or esters (Scheme 1a).4 Recently, Nishikata and coworkers reported copper-catalyzed oxyalkylation of alkenes to afford iminolactone by controlling the reactivity of the oxygen nucleophile of the amide group (Scheme 1b).5 However, these methods require long reaction time, anhydrous solvent, inert atmosphere protection and sometimes even special apparatuses such as the glovebox to manipulate the reactions. Therefore, a practical and simple methodology towards effective intermolecular oxyalkylation of alkenes is highly desirable. Recently, we developed selectuor-mediated highly selective radical dioxygenation of alkenes and metal-free catalyzed C-O bond formation reactions directly from C-H bonds.6 As part of our ongoing study on difunctionalization of alkenes 6a,d and C-O bond formation reactions, we present herein our recent progress in copper-catalyzed highly regioselective oxyalkylation of styrenes and readily available a-bromoacetamides under air.We started our investigation by applying styrene 1a and 2-bromo-2-methyl-N-phenylpropanamide 2a in a model reaction to optimize the reaction conditions. To our delight, in the preliminary experiment of using 10 mol% of CuI as catalyst, the desired oxyalkylation proceeded to give the desired product 3a in 45% yield in the presence of 1,