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Mechanistic insights into facilitating reductive elimination from Ni(II) species.
Chem Commun (Camb)
July 2024
College of Chemistry, and Pingyuan Laboratory, Zhengzhou University, Zhengzhou, Henan, 450001, P. R. China.
Reductive elimination is a key step in Ni-catalysed cross-couplings, which is often considered to result in new covalent bonds. Due to the weak oxidizing ability of Ni(II) species, reductive eliminations from Ni(II) centers are challenging. A thorough mechanistic understanding of this process could inspire the rational design of Ni-catalysed coupling reactions.
View Article and Find Full Text PDFInvestigating the mechanism of Ni-mediated trifluoromethylthiolation of aryl halides using AgSCF.
Dalton Trans
March 2023
Department of Chemistry, The University of British Columbia, Vancouver, BC, V6T 1Z1, Canada.
The mechanism of the Ni-catalysed trifluoromethylthiolation of aryl chlorides using AgSCF is studied herein. A variety of IPr Ni complexes were synthesized oxidative addition of Ni to 2-(2-chloro)phenylpyridines. Their reactivity with AgSCF was tested by performing stoichiometric experiments, cyclic voltammetry, and NMR spectroscopic studies.
View Article and Find Full Text PDFInsights into the mechanism and regioselectivity in Ni-catalysed redox-relay migratory hydroarylation of alkenes with arylborons.
Chem Commun (Camb)
December 2021
Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China.
DFT studies reveal that Ni-catalysed redox-relay hydroarylation of alkenes occurs concerted hydronickelation, iterative β-H elimination/migratory insertion and reductive elimination to yield the α-substituted product. The driving force for the redox-relay migratory hydroarylation arises from the stability of the LArNi(II)CHPhPr intermediate, which only allows its C-C elimination pathway to be opened up.
View Article and Find Full Text PDFThe Anionic Pathway in the Nickel-Catalysed Cross-Coupling of Aryl Ethers.
Angew Chem Int Ed Engl
November 2021
Departement für Chemie, Biochemie und Pharmazie, Universität Bern, Freiestrasse 3, 3012, Bern, Switzerland.
The Ni-catalysed cross-coupling of aryl ethers is a powerful method to forge new C-C and C-heteroatom bonds. However, the inert C(sp )-O bond means that a canonical mechanism that relies on the oxidative addition of the aryl ether to a Ni centre is thermodynamically and kinetically unfavourable, which suggests that alternative mechanisms may be involved. Here, we provide spectroscopic and structural insights into the anionic pathway, which relies on the formation of electron-rich hetero-bimetallic nickelates by adding organometallic nucleophiles to a Ni centre.
View Article and Find Full Text PDFThe pivotal role of electronics in preferred alkene over alkyne Ni-carboryne insertions and absolute regioselectivities.
Dalton Trans
May 2018
Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, China.
The in situ formation mechanisms of active Ni-carboryne species (COM1) and subsequent alkene/alkyne Ni-C bond insertion priorities, as well as relevant cycloaddition regioselectivities and kinetics, were investigated using the IDSCRF-B3LYP density functional theory (DFT) method, and all atoms were equitably treated at the DGDZVP level. The results reveal the o-carborane species to be energetically hedged into a four-step path (barrier heights 5.3, 19.
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