Synthesis of Imides by Palladium‐Catalyzed CH Functionalization of Aldehydes with Secondary Amides

Abstract

An efficient palladium-catalyzed C-H functionalization of aldehydes with various N-substituted N-heteroarene-2-carboxamides has been developed for the synthesis of secondary imides. The reaction tolerates various functionalities, such as methoxy, fluoro, chloro, and bromo groups. A tentative radical mechanism for a Pd(II)/Pd(IV) catalytic cycle is proposed.

Copper(II)-β-cyclodextrin immobilized on graphitic carbon nitride nanosheets as a highly effective catalyst for tandem oxidative amidation of benzylic alcohols

“…( o C) (Ref.) 1 a 95 108–110 50 2 a 90 162–164 51 3 a 95 101–103 52 4 a 93 132–134 53 5 a 75 139–142 54 6 a 65 95–97 55 7 b 90 160–162 56 8 b 85 200–202 57 9 …”

Palladium(II)‐Catalyzed Sp3/Sp2γ‐ and δ‐C‐H Functionalization of Aryl Amines using 5‐Methylisoxazole‐3‐Carboxamide as Directing Group

“…Initially, Huang's group used the MICA moiety for the preparation of a few examples of tertiary amides . In 2015 Liu et al.…”

Chemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions

“…It operates chemoselectively at room temperature in the presence of other functional groups, including carboxylic acids, alcohols, alkenes, and secondary amines. With slight modification of the reaction conditions, it can also be applied to the acylation of primary amides, ureas, sulfonamides, and carbamates, which are typically resistant to acylation under mild conditions …”

“…KATs having triple bonds ( 5l ), activated esters ( 5m ), azide groups ( 5n ), and coumarin-bearing KATs ( 5o ) afforded the corresponding imide in moderate to good yields. There are relatively few methods known for preparation of their mixed acyclic imides and related compounds, which are interesting components of bioactive natural products, pharmaceuticals, and catalysts. , …”