Redox-Neutral Palladium-Catalyzed C–H Functionalization To Form Isoindolinones with Carboxylic Acids or Anhydrides as Readily Available Starting Materials

Abstract

An operationally simple, Pd-catalyzed C-H functionalization is described for the synthesis of important and useful isoindolinones from readily available carboxamides and carboxylic acids or anhydrides. The reactions proceed efficiently with a broad range of substrates under redox-neutral reaction conditions and tolerate a diversity of functional groups. The mechanistic investigation suggests that the reactions involve C-H activation, nucleophilic addition, β-O elimination, and dehydration steps.

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

“…The formation of isoindolinones was reported by Wei using readily available reagents such as carboxylic acids or anhydrides as coupling partners ( Scheme 69A ). 420 In this process, the presence of an additional pivalic anhydride was required for the reaction with carboxylic acids.…”

Photocatalytic/Cu‐Promoted C−H Activations: Visible‐light‐Induced ortho‐Selective Perfluoroalkylation of Benzamides

“…Cu‐,– Pd‐, Ni‐, Co‐,– and Fe‐catalyzed or ‐mediated chelation‐assisted C−H bond activations to construct C−C and C−X bonds (X=S, O, N, F) [Eq. (1)] with the aid of an 8‐aminoquinoline directing group have been developed by the groups of Daugulis, Hirano, and Miura,– Ge, Kuninobu and Kanai,, Stahl, Chatani,,– and others ––. Ours and other groups also independently developed the selective ortho ‐sulfonylation and nitration of benzamides bearing the 8‐aminoquinoline group .…”

Alkali‐Metal Promoted Chemo‐ and Regioselective Cycloisomerization Reactions to (Z)‐3‐Alkylideneisoindolin‐1‐ones: Unusual Positive Role of H2O

“…However, the chemo‐ and/or regioselectivity of these transformations are always the key issue in terms of the structure of the final heterocyclic products (Scheme ). For example, although most of the transition‐metal‐catalyzed methods presented above are the formation of the exo‐type heterocycles, the endo‐type cyclizations can be observed in some cases ,,…”