22980-76-3

Basic information

• Product Name: NiCl₂(1,10-phenanthroline)
• Synonyms: NiCl₂(1,10-phenanthroline)
• CAS NO: 22980-76-3
• Molecular Weight: 309.805
• Mol File: 22980-76-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: NiCl₂(1,10-phenanthroline)(CAS DataBase Reference)
• NIST Chemistry Reference: NiCl₂(1,10-phenanthroline)(22980-76-3)
• EPA Substance Registry System: NiCl₂(1,10-phenanthroline)(22980-76-3)

Safety Data

• Hazardous Substances Data: 22980-76-3(Hazardous Substances Data)

Upstream product

• 14783-10-9 [palladium(II)dichloride(1,10-phenanthroline)] 
• 15748-05-7 dichlorobis(1,10-phenanthroline)nickel(II) 
• 66-71-7 1,10-Phenanthroline 
• 83864-14-6 nickel dichloride 
• 29046-78-4 (1,2-dimethoxyethane)dichloronickel(II) 

Downstream Products

• 83864-14-6 nickel dichloride 
• 436154-25-5 Ni[PC₆H₅(C₆H₄S)2](1,10-phenanthroline) 

Relevant articles and documents

Mechanism of Nickel(II)-Catalyzed C(2)-H Alkynylation of Indoles with Alkynyl Bromide

The nickel system (THF)2NiBr2/phen has recently been shown as an efficient catalyst for the C-H bond alkynylation of diverse heteroarenes with (triisopropylsilyl)alkynyl bromide via monodentate chelation assistance. Herein, we report an extensive mechanistic investigation for the direct alkynylation of indoles involving the well-defined nickel catalyst, which features a coordinative insertion pathway of alkynyl bromide with the Ni(II) catalyst. Catalytic relevant nickel complexes, (phen)NiCl2 (5), (phen)2NiCl2 (6) and [(phen)3Ni]·NiCl4 (7) were isolated, and the complexes 6 and 7 were structurally characterized. Well-defined complexes were as competent as the in situ generated catalyst system (THF)2NiBr2/phen for the alkynylation of indoles. Various controlled studies and reactivity experiments were performed to understand the probable pathway for the alkynylation reaction. Kinetics analysis highlights that the complex (phen)NiX2 acts as a precatalyst, and the involvement of substrate indole and LiOtBu are essential for the generation of the active catalyst. Deuterium labeling and kinetic studies suggest that the process involving C-H cleavage and carbo-nickelation of indole is a crucial rate influencing step. Reactivity study of various alkynyl compounds with nickel-species highlights a migratory insertion route for the reaction. DFT calculations firmly support the experimental findings and suggest the coordinative insertion pathway of alkynyl bromide rather than oxidative addition toward the nickel(II) center.

Binuclear complex as well as preparation method and application thereof

The invention discloses a binuclear complex and a preparation method and application thereof. The binuclear complex comprises a structure shown in the following formula I or a structure shown in the following formula II shown in the specification, wherein M is a cobalt atom or a nickel atom. The invention provides a binuclear complex water oxidation catalyst with a novel structure, the water oxidation catalyst does not contain noble metals, and the prepared catalyst has good catalytic activity while the use of the noble metals is avoided, and has a good application prospect in the aspect of water oxidation catalysis.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.