Synthesis of 3-Acyl-2-arylindole via Palladium-catalyzed Isocyanide Insertion and Oxypalladation of Alkyne

Abstract

The synthesis of 3-acyl-2-arylindole derivatives was performed through palladium-catalyzed isocyanide insertion and oxypalladation of an alkyne. As a result of the introduction of internal nucleophiles, domino cyclization was also achieved for the synthesis of several tetracyclic indole derivatives. Imidoylpalladium generated by isocyanide insertion is a key intermediate in these reactions.

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

“…There are numerous reports in the literature regarding the utility of isocyanide chemistry for synthesis of various indole derivatives [157][158][159][160][161][162][163][164][165][166][167][168][169][170] …”

Palladium(0)-Catalyzed Benzylic C(<i>sp</i>³)–H Functionalization for the Concise Synthesis of Heterocycles and Its Applications

“…36) We also developed a new method for the synthesis of indoloquinazolinones and indoloquinazolinediones based on benzylic C(sp 3 )-H functionalization. 38) In both cases, the presence of an additional ortho substituent was important to the success of the reaction.…”

“…In this review, we provide a summary of our recent research on the Pd(0)-catalyzed benzylic C(sp 3 )-H functionalization reaction and its application. [33][34][35][36][37][38][39][40][41][42][43] 2. Pd-Catalyzed Benzylic C(sp 3 …”

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

“…(53)]. [88] Electron-donating groups and chlorine substituents within the aryl iodide 227a , have minimal effects on the reaction. Electron-withdrawing substituents cause a distinct decrease in the yield of the indole 229 .…”