N-Alkylation of organonitrogen compounds catalyzed by methylene-linked bis-NHC half-sandwich ruthenium complexes. Issue 4 (12th January 2022)

• Record Type: Journal Article
• Authors: Moutaoukil, Zakaria; Serrano-Díez, Emmanuel; Collado, Isidro G.; Jiménez-Tenorio, Manuel; Botubol-Ares, José Manuel
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 4(2022)
• Page Start: 831
• Page End: 839
• Publication Date: 2022-01-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02214h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient and scalable Ru-catalysed N -alkylation of amines, amides and sulfonamides with alcohols has been developed. Abstract : An efficient ruthenium-catalyzed N -alkylation of amines, amides and sulfonamides has been developed employing novel pentamethylcyclopentadienylruthenium(ii ) complexes bearing the methylene linked bis(NHC) ligand bis(3-methylimidazol-2-ylidene)methane. The acetonitrile complex 2 has proven particularly effective with a broad range of substrates with low catalyst loading (0.1–2.5 mol%) and high functional group tolerance under mild conditions. A total of 52 N -alkylated organonitrogen compounds including biologically relevant scaffolds were synthesized from (hetero)aromatic and aliphatic amines, amides and sulfonamides using alcohols or diols as alkylating agents in up to 99% isolated yield, even on gram-scale reactions. In the case of sulfonamides, it is the first example of N -alkylation employing a transition-metal complex bearing NHC ligands.