28796-12-5

Basic information

• Product Name: (CO)2Ni(P(C₆H₁₁-cyclo)3)2
• Synonyms: (CO)2Ni(P(C₆H₁₁-cyclo)3)2
• CAS NO: 28796-12-5
• Molecular Weight: 675.578
• Mol File: 28796-12-5.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (CO)2Ni(P(C₆H₁₁-cyclo)3)2(CAS DataBase Reference)
• NIST Chemistry Reference: (CO)2Ni(P(C₆H₁₁-cyclo)3)2(28796-12-5)
• EPA Substance Registry System: (CO)2Ni(P(C₆H₁₁-cyclo)3)2(28796-12-5)

Safety Data

• Hazardous Substances Data: 28796-12-5(Hazardous Substances Data)

Upstream product

• 1295-35-8 bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ 
• 692-45-5 vinyl formate 
• 2622-14-2 tricyclohexylphosphine 
• 108-98-5 thiophenol 
• 201230-82-2 carbon monoxide 
• 57307-01-4 (P(C₆H₁₁)3)2Ni*CO₂ = (P(C₆H₁₁)3)2Ni(CO₂) 
• 82384-39-2 trans-NiH(succinimido)((C₆H₁₁)3P)2 
• 1295-35-8 bis(1,5-cyclooctadiene)nickel⁽⁰⁾ 
• 455-32-3 benzoyl fluoride 
• 380499-25-2 Ni(PCy₃)2(cod) 
• 1333166-43-0 (S)-5-benzyl-1,3-dioxolane-2,4-dione 
• 41685-59-0 ethene-bis(tricyclohexylphosphane)-nickel(0) 
• 613-90-1 benzoyl cyanide 
• 36568-49-7 Ni(P(C6H11-cyclo)3)2 

Downstream Products

• 53323-82-3 ((CH₃)2C(CH₂OP(OCH₂)2C(CH₃)2)2)Ni(P(C₆H₁₁-cyclo)3)2 

Relevant articles and documents

Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides

This Article describes the development of a base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products. Detailed studies were conducted to assess the relative rates of direct transmetalation between aryl boronate esters and diboron reagents and a bisphosphine nickel(aryl)(fluoride) intermediate. These investigations revealed that diboron reagents undergo transmetalation with this Ni(aryl)(fluoride) intermediate at rates significantly faster than their aryl boronate ester congeners. Furthermore, the reactivity of both boron reagents toward transmetalation is enhanced with increasing electrophilicity of the boron center. These mechanistic insights were leveraged to develop a catalytic decarbonylative borylation of acid fluorides that proved applicable to a variety of (hetero)aryl carboxylic acid fluorides as well as diverse diboron reagents. The acid fluorides can be generated in situ directly from carboxylic acids. Furthermore, the mechanistic studies directed the identification of various air-stable Ni pre-catalysts for this transformation.

Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids

A variety of functionalized biaryls can be accessed by coupling aryl and heteroaryl esters with boronic acids in Suzuki-Miyaura-type decarbonylative cross-coupling catalyzed by an affordable catalyst system composed of Ni(cod)2 and PCy3. The methodology is tolerant of a variety of functional groups and presents an attractive alternative to the use of palladium catalysis currently used in industry to acquire such bis(hetero)aryls, but also reveals challenges associated with nickel catalysis of esters in cross-coupling chemistry.

Bioinorganic chemistry of nickel and carbon dioxide: An Ni complex behaving as a model system for carbon monoxide dehydrogenase enzyme

In this paper we report the results of our studies on Ni complexes, the chemistry of which is relevant to the carbon monoxide dehydrogenase (CODH) enzyme of acetogenic bacteria. A single Ni system is able to promote both the reduction of carbon dioxide to carbon monoxide and the subsequent coupling of bound CO with an olefin and a thio group to afford an organic thioester, mimicking the enzyme activity.