A Visible Light‐Mediated Regioselective Halogenation of Anilides and Quinolines by Using a Heterogeneous Cu‐MnO Catalyst

Abstract

A simple and practical heterogeneous Cu‐MnO catalyzed regioselective halogenation of anilides and quinolines under irradiation with household 40 W incandescent lamp was developed. This method uses a recyclable Cu‐MnO catalyst, acetonitrile as an industrially friendly solvent, and economic N‐halo succinimides as a halogenating source. The reaction is scalable and well tolerated with a broad range of functional groups.

Room-Temperature Synthesis of Isoindolone Spirosuccinimides: Merger of Visible-Light Photocatalysis and Cobalt-Catalyzed C–H Activation

“…In 3d series metallophotocatalysis, nickel/photo redox, copper/photo redox, and cobalt/photoredox catalytic systems have showcased several challenging direct C–C and C-heteroatom bond formation reactions under mild reaction conditions. Sundararaju and coworkers reported C–H and N–H bond annulation with alkene, any alkyne by merging cobalt catalyst with a suitable photocatalyst (Scheme c). , Along the same lines, in our continuous effort to develop a sustainable catalytic system for the C–H functionalization reaction, we herein report a readily available Co-catalyst, Co­(acac) 2 , in combination with a commonly available organic dye, Eosin-Y, as a photocatalyst provided isoindolone spirosuccinimides in good to excellent yields by oxidative cyclization of benzamides with maleimides via 8-aminoquinoline directed C–H activation at room temperature and without any sacrificial metal oxidant.…”

Visible-Light-Induced Catalytic Selective Halogenation with Photocatalyst

“…In 2018, Ghosh and co-workers reported extensive application of Cu-MnO catalyst for halogenations of anilides and quinolones [ 50 ]. They used Cu-MnO as a catalyst and N -halosuccinimide as a halogenating source in acetonitrile under visible light irradiation to achieve halogenations of anilides and quinolines with good regioselectivity ( Scheme 43 and Scheme 44 ).…”

Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

“…1 H NMR (400 MHz, CDCl 3 ):  = 7.75 (s, 1 H), 7.47 (br s, 1 H), 7.40 (d, J = 7.9 Hz, 1 H), 7.24-7.14 (m, 2 H), 2.17 (s, 3 H). N-(2,4-Dichlorophenyl)acetamide (3n) 14 Yield: 87 mg (85%); brown solid; mp 144-145 °C. 1…”