447405-44-9

Upstream product

• 1295-35-8 bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ 
• 1437769-72-6 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate 
• 7550-35-8 lithium bromide 
• 2622-14-2 tricyclohexylphosphine 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 36673-36-6 dibromobis(triphenylphosphine)nickel(II) 
• 269410-06-2 2-(2-bromophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 447405-43-8 [NiBr(o-C₆H₄B(pinacolate))(PPh₃)2] 

Downstream Products

• 447405-55-2 [Ni(η2-C6H4)(P(C6H11)3)2] 
• 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) 
• 114907-51-6 [η²-benzyne][1,2-bis(dicyclohexylphosphino)ethane]nickel(0) 

Relevant academic research and scientific papers

Preparation of Aryne-Nickel Complexes from ortho-Borylaryl Triflates

A facile method for preparing diverse aryne-nickel complexes from readily synthesized ortho-borylaryl triflates is described. Exploratory synthetic applications, including the synthesis of 1,2-difunctionalized arenes, based on the nucleophilic character of the aryne-nickel complexes are also demonstrated.

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.