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Unifying -Sulfinylamines with Alkyltrifluoroborates by Organophotoredox Catalysis: Access to Functionalized Alkylsulfinamides and High-Valent S(VI) Analogues.
Org Lett
May 2024
School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, Thiruvananthapuram 695551, Kerala, India.
We describe an organophotoredox-catalyzed sp C-S coupling of -sulfinylamines with bench-stable alkyltrifluoroborates as a latent nucleophilic counterpart en route to alkylsulfinamides in high efficiency. In contrast to the two-electron reactivity of traditional organometallic reagents, this catalytic method reports the single-electron process of an organometallic reagent with -sulfinylamines in C-S coupling. This mild and scalable protocol offers operational simplicity and exceptional functional group compatibility, including ketone, ester, amide, nitrile, and halides, that is vulnerable to organolithium or Grignard reagents.
View Article and Find Full Text PDFNitrenium ions as new versatile reagents for electrophilic amination.
Chem Sci
November 2023
Schulich Faculty of Chemistry, Technion - Israel Institute of Technology Technion City Haifa 32000 Israel
Herein we report the utilization of N-heterocyclic nitrenium ions - easily prepared, bench-stable and non-oxidating nitrogen sources for the efficient electrophilic amination of aliphatic and aromatic organometallic nucleophiles, towards the facile and general preparation of primary amines. To this end, a plethora of abundant organolithium and organomagnesium reagents were combined with nitrenium salts to generate a variety of previously unexplored -alkyl and -aryl triazanes. Through the simple hydrogenolysis of these relatively stable triazanes, we have prepared a diverse scope of primary amines, including linear and branched aliphatic as well as (hetero)aromatic amines possessing various stereo-electronic substituents.
View Article and Find Full Text PDFAn Experimental and Computational Investigation Rules Out Direct Nucleophilic Addition on the N Ligand in Manganese Dinitrogen Complex [Cp(CO) Mn(N )].
Angew Chem Int Ed Engl
October 2023
LCC-CNRS, Université de Toulouse, CNRS, UPS, 205 route de Narbonne, BP44099, 31077, Toulouse cedex 4, France.
We have re-examined the reactivity of the manganese dinitrogen complex [Cp(CO) Mn(N )] (1, Cp=η -cyclopentadienyl, C H ) with phenylithium (PhLi). By combining experiment and density functional theory (DFT), we have found that, unlike previously reported, the direct nucleophilic attack of the carbanion onto coordinated dinitrogen does not occur. Instead, PhLi reacts with one of the CO ligands to provide an anionic acylcarbonyl dinitrogen metallate [Cp(CO)(N )MnCOPh]Li (3) that is stable only below -40 °C.
View Article and Find Full Text PDFStable organolithium gels.
Nat Chem
March 2023
Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, Bern, Switzerland.
Iron Catalysis: A New Horizon Towards Organoboron-mediated C-C Cross-coupling.
Chem Asian J
December 2022
Department of Chemistry, Indian Institute of Technology, 721302, Kharagpur, India.
Transition metal-catalyzed cross-couplings have had a profound impact on chemical synthesis. Among the various transition metals, iron has drawn huge attention due to its cost effectiveness, range of stable oxidation states, Lewis acidic property and releatively less toxicity. Iron complexes have exhibited an efficient catalytic activity towards the cross-coupling reaction using organomagnesium, organolithium and organozinc reagent.
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