117788-16-6Relevant articles and documents
Assembly of Indole Cores through a Palladium-Catalyzed Metathesis of Ar-X σ-Bonds
Ferrier, Robert C.,Ghasemi, Mehran,Habibi, Azizollah,Jafarpour, Farnaz,Navid, Hamed,Rajai-Daryasarei, Saideh,Safaie, Niloofar
, p. 9556 - 9561 (2020)
We describe the development of a new method for construction of highly substituted indole scaffolds through the strategic utilizing of the metathesis of Ar-X σ-bonds based on the dynamic nature of palladium-based oxidative addition/reductive elimination. A suitable and simple catalytic system has provided an appropriate platform for a productive ligand exchange and consecutive carbopalladation/C-H activation/amination of phosphine ligands with alkynes and aromatic/aliphatic amines for construction of structurally diverse indoles.
Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy
Shang, Yaping,Jonnada, Krishna,Yedage, Subhash Laxman,Tu, Hua,Zhang, Xiaofeng,Lou, Xin,Huang, Shijun,Su, Weiping
supporting information, p. 9547 - 9550 (2019/08/15)
Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.
Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles
Zhou, Shuguang,Wang, Jinhu,Wang, Lili,Chen, Kehao,Song, Chao,Zhu, Jin
supporting information, p. 3806 - 3809 (2016/08/16)
A Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C-H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of an acetylenic unit through C2-desilylation on a C2-silylated indole derivative, formal inversion of regioselectivity through consecutive C3-derivatization and C2-desilylation processes, and formal bond migration for a linear-chain terminal alkyne.