447405-43-8

Basic information

• Product Name: [NiBr(o-C₆H₄B(pinacolate))(PPh₃)2]
• Synonyms: [NiBr(o-C₆H₄B(pinacolate))(PPh₃)2]
• CAS NO: 447405-43-8
• Molecular Weight: 866.245
• Mol File: 447405-43-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [NiBr(o-C₆H₄B(pinacolate))(PPh₃)2](CAS DataBase Reference)
• NIST Chemistry Reference: [NiBr(o-C₆H₄B(pinacolate))(PPh₃)2](447405-43-8)
• EPA Substance Registry System: [NiBr(o-C₆H₄B(pinacolate))(PPh₃)2](447405-43-8)

Safety Data

• Hazardous Substances Data: 447405-43-8(Hazardous Substances Data)

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 36673-36-6 dibromobis(triphenylphosphine)nickel(II) 
• 269410-06-2 2-(2-bromophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 

Downstream Products

• 447405-53-0 [Ni(η2-C6H4)(PPh3)2] 
• 447405-45-0 trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(triethylphosphine)]nickel(II) 
• 447405-48-3 [NiBr(o-C₆H₄B(pinacolate))(1,2-bis(diphenylphosphino)butane)] 
• 447405-44-9 trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II) 
• 447405-46-1 cis-bromo[1,2-bis(dicyclohexylphosphino)ethane][2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]nickel(II) 
• 447405-47-2 [NiBr(o-C₆H₄B(pinacolate))(1,2-bis(diphenylphosphino)ethane)] 
• 447405-56-3 [Ni(η2-C6H4)(1,2-bis(diphenylphosphino)ethane)] 
• 473829-82-2 [NiBr(C₆H₅)(1,2-bis(dicyclohexylphosphino)ethane)] 
• 447405-55-2 [Ni(η2-C6H4)(P(C6H11)3)2] 
• 114907-51-6 [η²-benzyne][1,2-bis(dicyclohexylphosphino)ethane]nickel(0) 

Relevant articles and documents

Preparation of benzyne complexes of group 10 metals by intramolecular Suzuki coupling of ortho-metalated phenylboronic esters: Molecular structure of the first benzyne-palladium(0) complex

A series of nickel(II) and palladium(II) aryl complexes substituted in the ortho position of the aromatic ring by a (pinacolato)boronic ester group, [MBr{o-C6H4B(pin)}L2] (M = Ni, L2 = 2PPh3 (2a), 2PCy3 (2b), 2PEt3 (2c), dcpe (2d), dppe (2e), and dppb (2f); M = Pd, L2 = 2PPh3 (3a), 2PCy3 (3b), and dcpe (3d)), has been prepared. Many of these complexes react readily with KOtBu to form the corresponding benzyne complexes [M(η2-C6H4)L2] (M = Ni, L2 = 2PPh3 (4a), 2PCY3 (4b), 2PEt3 (4c), dcpe (4d); M = Pd, L2 = 2PCy3 (5b)). This reaction can be regarded as an intramolecular version of a Suzuki cross-coupling reaction, the driving force for which may be the steric interaction between the boronic ester group and the phosphine ligands present in the precursors 2 and 3. Complex 3d also reacts with KOtBu, but in this case disproportionation of the initially formed η2-C6H4 complex (5d) leads to a 1:1 mixture of a novel dinuclear palladium(I) complex, [(dcpe)Pd(μ2-C6H4)Pd(dcpe)] (6), and a 2,2′-biphenyldiyl complex, [Pd(2,2′-C6H4C6H4)-(dcpe)] (7d). Complexes 2a, 3b, 3d, 4b, 5b, 6, and 7d have been structurally characterized by X-ray diffraction; complex 5b is the first example of an isolated benzyne-palladium(0) species.