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Direct Access to meta‐Alkylated N‐Arylazolium Salts via Ruthenium Catalyzed Electronically Controlled Site Selective Functionalization: Scope and Mechanistic Aspect.
- Source :
-
Advanced Synthesis & Catalysis . 7/18/2023, Vol. 365 Issue 14, p2385-2391. 7p. - Publication Year :
- 2023
-
Abstract
- Effective access to azolium salts with varying stereoelectronic properties has always fascinated the organometallic chemists. Herein, we described a Ru(II)‐catalyzed one‐step access to diverse meta‐alkylated N‐aryl (benz)imidazolium salts (>40 examples) via σ‐bond activation strategy starting from the readily available azolium salts using alkyl bromide. Notably, the present method is compatible with a wide range of azolium salts and secondary/tertiary alkyl bromides, including the biologically relevant motifs. Various control experiments along with the DFT calculation established the reaction pathway of orthometalated Ru(II)‐NHC complex (6) formation followed by the generation of a Ru(III)‐intermediate, which controls the observed meta‐selectivity, via single electron transfer. Crucially, detailed insight of the reaction mechanism helped to comprehend why some substrates are challenging for this methodology. [ABSTRACT FROM AUTHOR]
- Subjects :
- *RUTHENIUM
*ALKYL bromides
*CHARGE exchange
*SALT
*SALTS
Subjects
Details
- Language :
- English
- ISSN :
- 16154150
- Volume :
- 365
- Issue :
- 14
- Database :
- Academic Search Index
- Journal :
- Advanced Synthesis & Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 167301081
- Full Text :
- https://doi.org/10.1002/adsc.202300392