Electrochemistry-enabled Ir-catalyzed C-H/N-N bond activation facilitates [3+2] annulation of phenidones with propiolates.

Chem Commun (Camb)

Institute of Medicine and Materials Applied Technologies, College of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165, China.

Published: January 2025

A mild and efficient [3+2] annulation of phenidones with propiolates has been developed to access -substituted indole alkylamides, enabled by merging electrochemistry with iridium catalysis using an undivided cell at room temperature. The mechanistic studies have confirmed that the electrochemically mediated catalytic cycle of Ir-Ir-Ir exhibits enhanced efficiency, mild reaction conditions, and unconventional selectivity.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d4cc03124eDOI Listing

Publication Analysis

Top Keywords

[3+2] annulation
8
annulation phenidones
8
phenidones propiolates
8
electrochemistry-enabled ir-catalyzed
4
ir-catalyzed c-h/n-n
4
c-h/n-n bond
4
bond activation
4
activation facilitates
4
facilitates [3+2]
4
propiolates mild
4

Similar Publications

Electrochemistry-enabled Ir-catalyzed C-H/N-N bond activation facilitates [3+2] annulation of phenidones with propiolates.

Chem Commun (Camb)

January 2025

Institute of Medicine and Materials Applied Technologies, College of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165, China.

A mild and efficient [3+2] annulation of phenidones with propiolates has been developed to access -substituted indole alkylamides, enabled by merging electrochemistry with iridium catalysis using an undivided cell at room temperature. The mechanistic studies have confirmed that the electrochemically mediated catalytic cycle of Ir-Ir-Ir exhibits enhanced efficiency, mild reaction conditions, and unconventional selectivity.

View Article and Find Full Text PDF

A Facile Approach to Tetracyclic Indolines: Highly Diastereoselective [4+2] Annulation of Indoles with Bicyclic N-Substituted Cyclobutanes.

J Org Chem

January 2025

Chang-Kung Chuang Institute, Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, College of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.

A new stereoselective [4+2] annulation method for constructing tetracyclic indolines by reacting indoles with bicyclic N-substituted cyclobutanes has been developed. Using Sc(OTf) as a catalyst, a series of tetracyclic indolines with four continued stereogenic carbon centers have been obtained in ≤86% yields as single diastereomers. This reaction offers an accessible way for the rapid construction of the core structures of biologically active natural products like paucidirinine, deethylibophyllidine, and ibophyllidine.

View Article and Find Full Text PDF

The first carbocyclic gallylene [(ADC)Ga(GaI)] and bis-gallylene [(ADC)Ga] (ADC = PhC{N(Dipp)C}; Dipp = 2,6-iPrCH) featuring a central CGa ring annulated between two 1,3-imidazole rings are prepared by KC reductions of [(ADC)GaI]. Treatment of [(ADC)Ga] with Fe(CO) affords complex [(ADC)GaFe(CO)] in which each Ga(i) atom serves as a two-electron donor. [(ADC)Ga] activates white phosphorus (P) and the C -F bond of aryl fluorides (ArF) to yield compounds [(ADC)Ga(P)] and -/-[(ADC)GaF(Ar)], respectively.

View Article and Find Full Text PDF

Condition-Controlled Rh(III)-Catalyzed Chemodivergent Cyclization of 2-Arylpyridines with CF-Imidoyl Sulfoxonium Ylides via Triple C-H Activation.

Org Lett

January 2025

Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Provincial Key Laboratory of Research and Development on Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, China.

A condition-controlled Rh(III)-catalyzed selective synthesis of CF-substituted indoles and pyrido[2,1-]isoindoles from 2-arylpyridines and CF-imidoyl sulfoxonium ylides has been developed. The Cp*Rh(MeCN)(SbF)/HFIP system afforded CF-substituted indoles via triple C-H activation, while the [Cp*RhCl]/MeCN condition selectively furnished CF-substituted pyrido[2,1-]isoindoles through C-H [4 + 1] annulation. The notable advantages of this developed method included readily available starting materials, broad substrate scope, and excellent chemoselectivity.

View Article and Find Full Text PDF

Dirhodium-Palladium Dual-Catalyzed [1 + 1 + 3] Annulation to Heterocycles Using Primary Amines or HO as the Heteroatom Sources.

J Am Chem Soc

January 2025

State Key Laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

The ever-increasing demand in chemical biology and medicinal research requires the development of new synthetic methods for the rapid construction of libraries of heterocycles from simple raw materials. In this context, the utilization of primary amines or HO as the simple - or -sources in the assembly of a heterocyclic ring skeleton is highly desirable from the viewpoint of atom- and step-economy. Herein, we describe a highly efficient three-component reaction of diazo, allylic diacetates, and commercially available anilines (or HO) to access structurally diverse pyrrolidine and tetrahydrofuran derivatives.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!