1034901-50-2

Basic information

• Product Name: NiCl2dtbbpy
• CAS NO: 1034901-50-2
• Molecular Weight: 397.998
• Mol File: 1034901-50-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: >300 °C
• CAS DataBase Reference: NiCl2dtbbpy(CAS DataBase Reference)
• NIST Chemistry Reference: NiCl2dtbbpy(1034901-50-2)
• EPA Substance Registry System: NiCl2dtbbpy(1034901-50-2)

Safety Data

• Hazardous Substances Data: 1034901-50-2(Hazardous Substances Data)

Usage

Description

NiCl2dtbbpy, also known as [4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride, is a coordination compound that consists of a nickel (II) ion coordinated to a dtbbpy ligand. It is a versatile catalyst with unique catalytic properties, making it suitable for various organic reactions.

Uses

Used in Organic Synthesis:
NiCl2dtbbpy is used as a catalyst for various organic reactions, enhancing the efficiency and selectivity of the processes. Its applications include:
1. Decarboxylative Arylation of Oxo Acids:
NiCl2dtbbpy is used as a catalyst in the decarboxylative arylation of oxo acids, enabling the formation of aryl ketones through a single-step process. This method is advantageous due to its atom economy and mild reaction conditions.
2. Acylation of Ethers:
In the acylation of ethers, NiCl2dtbbpy serves as a catalyst, promoting the formation of aryl ether products. This reaction is significant for the synthesis of various organic compounds and pharmaceuticals.
3. Cross-Coupling of Aryl Bromides with Alcohols:
NiCl2dtbbpy is employed as a catalyst in the cross-coupling of aryl bromides with alcohols, facilitating the formation of aryl ethers. This reaction is crucial for the synthesis of complex organic molecules and the development of new materials.
Overall, NiCl2dtbbpy is a valuable catalyst in the field of organic synthesis, offering a range of applications across different industries, including pharmaceuticals, materials science, and chemical research.

Upstream product

• 72914-19-3 4,4'-di-tert-butyl-2,2'-bipyridine 
• 83864-14-6 nickel dichloride 
• 29046-78-4 (1,2-dimethoxyethane)dichloronickel(II) 
• 76-83-5 trityl chloride 

Relevant articles and documents

Long-Lived Charge-Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer

Here we investigate the photophysics and photochemistry of Ni(II) aryl halide complexes common to cross-coupling and Ni/photoredox reactions. Computational and ultrafast spectroscopic studies reveal that these complexes feature long-lived 3MLCT excited states, implicating Ni as an underexplored alternative to precious metal photocatalysts. Moreover, we show that 3MLCT Ni(II) engages in bimolecular electron transfer with ground-state Ni(II), which enables access to Ni(III) in the absence of external oxidants or photoredox catalysts. As such, it is possible to facilitate Ni-catalyzed C-O bond formation solely by visible light irradiation, thus representing an alternative strategy for catalyst activation in Ni cross-coupling reactions.

Photoredox Nickel-Catalyzed C-S Cross-Coupling: Mechanism, Kinetics, and Generalization

Photoredox-mediated nickel-catalyzed cross-couplings have evolved as a new effective strategy to forge carbon-heteroatom bonds that are difficult to access with traditional methods. Experimental mechanistic studies are challenging because these reactions involve multiple highly reactive intermediates and perplexing reaction pathways, engendering competing, but unverified, proposals for substrate conversions. Here, we report a comprehensive mechanistic study of photoredox nickel-catalyzed C-S cross-coupling based on time-resolved transient absorption spectroscopy, Stern-Volmer quenching, and quantum yield measurements. We have (i) discovered a self-sustained productive Ni(I/III) cycle leading to a quantum yield φ > 1; (ii) found that pyridinium iodide, formed in situ, serves as the dominant quencher for the excited state photocatalyst and a critical redox mediator to facilitate the formation of the active Ni(I) catalyst; and (iii) observed critical intermediates and determined the rate constants associated with their reactivity. Not only do the findings reveal a complete reaction cycle for C-S cross-coupling, but the mechanistic insights have also allowed for the reaction efficiency to be optimized and the substrate scope to be expanded from aryl iodides to include aryl bromides, thus broadening the applicability of photoredox C-S cross-coupling chemistry.

Synthesis and Reactivity of Paramagnetic Nickel Polypyridyl Complexes Relevant to C(sp2)–C(sp3)Coupling Reactions

A number of new transition metal catalyzed methods for the formation of C(sp2)–C(sp3) bonds have recently been described. These reactions often utilize bidentate polypyridyl-ligated Ni catalysts, and paramagnetic NiI halide or aryl species are proposed in the catalytic cycles. However, there is little knowledge about complexes of this type. Here, we report the synthesis of paramagnetic bidentate polypyridyl-ligated Ni halide and aryl complexes through elementary reactions proposed in catalytic cycles for C(sp2)–C(sp3) bond formation. We investigate the ability of these complexes to undergo organometallic reactions that are relevant to C(sp2)–C(sp3) coupling through stoichiometric studies and also explore their catalytic activity.