Synthesis of Substituted Carbazoles by a Vinylic to Aryl Palladium Migration Involving Domino C−H Activation Processes

2005/01/20 by Jian Zhao, Richard C. Larock · 2 citations
Chemistry · #Catalytic C–H Functionalization Methods #Catalytic Cross-Coupling Reactions #Oxidative Organic Chemistry Reactions

paper · doi:10.1021/ol0474655

openalex publication_date 2005/01/20 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

Substituted carbazoles are readily prepared in good yields by the palladium-catalyzed cross-coupling of alkynes and N-(3-iodophenyl)anilines. This process proceeds by carbopalladation of the alkyne, heteroatom-directed vinylic to aryl palladium migration, and ring closure involving two consecutive C-H activation processes. The process has also been expanded to the synthesis of an indole. [Structure: see text]

Citations

• Pd-Catalyzed Alkyl to Aryl Migration and Cyclization: An Efficient Synthesis of Fused Polycycles via Multiple C−H Activation
• C−H Activation and Palladium Migration within Biaryls under Heck Reaction Conditions

Cited by

• Nota non titolata a Cons. Stato, 3 marzo 2001, n. 1948 e 12 aprile 2001, n. 2247
• Carboxylate-Assisted Transition-Metal-Catalyzed C−H Bond Functionalizations: Mechanism and Scope
• Organopalladium chemistry [wikipedia]