1246183-55-0

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 3188-13-4 ethyl chloromethyl ether 
• 153625-67-3 1,2-bis-[(2,6-diisopropylphenyl)imino]acenaphthene 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 82-86-0 acenaphthene quinone 

Downstream Products

• 1246183-56-1 IPr(BIAN) 
• 1616954-85-8 (7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium)copper(I) chloride 

Relevant academic research and scientific papers

Physical and photophysical properties of a linear copper(I) complex of a bulky acenapthene-based NHC ligand

We report the first example of a charge-neutral linear two-coordinate copper(I) complex bearing a sterically demanding acenaphthoimidazolylidene-based N-heterocyclic carbene (NHC) ligand. The identity and geometry of the complex are confirmed by single-crystal X-ray diffraction (XRD) analysis. The complex is poorly emissive at room temperature, showing either ligand-centered (LC) emission around 340 nm when excited at 300 nm or ligand-to-ligand charge transfer (LLCT) emission at 540 nm when excited at 420 nm; in chloroform, dual emission is observed upon photoexcitation at 300 nm. Nanosecond emission lifetimes were recorded for these processes. This is the first example of emissive linear copper(I) complexes containing this bulky NHC ligand.

Antimicrobial properties of some bis(iminoacenaphthene (BIAN)-supported N-heterocyclic carbene complexes of silver and gold

The AgCl, AgOAc, AuCl, and AuOAc complexes of the new bis(imino) acenaphthene(BIAN)-supported N-heterocyclic carbene ligand and the precursor imidazolium salt have been investigated with respect to their antimicrobial activities against Staphylococcus aur

Robust Buchwald-Hartwig amination enabled by ball-milling

An operationally simple mechanochemical method for the Pd catalysed Buchwald-Hartwig amination of arylhalides with secondary amines has been developed using a Pd PEPPSI catalyst system. The system is demonstrated on 30 substrates and applied in the context of a target synthesis. Furthermore, the performance of the reaction under aerobic conditions has been probed under traditional solution and mechanochemical conditions, the observations are discussed herein.

Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling

A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross-coupling reaction via mechanochemical methods is reported. The reported method exhibits a broad substrate scope for both C(sp3)–C(sp2) and C(sp2)–C(sp2) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in situ generation organometallic compounds from base metals and their concomitant engagement in synthetic reactions via mechanochemical methods.

Mild negishi cross-coupling reactions catalyzed by acenaphthoimidazolylidene palladium complexes at low catalyst loadings

Considering that the strong σ-donor property of ylidenes derived from π-extended imidazolium salts is conducive to increasing the catalytic activity of the resulting palladium N-heterocyclic carbene complexes, robust acenaphthoimidazol-ylidene palladium complexes 3a-c with varying bulky substituted groups were prepared from the corresponding acenaphthoimidazolium chlorides by heating with PdCl2 and K2CO3 in neat 3-chloropyridine in satisfactory yields. Even at a catalyst loading as low as 0.25 mol %, complex 3a exhibited extremely high catalytic activity toward Negishi cross-coupling of alkylzinc reagents with a wide range of (hetero)aryl halides under mild reaction conditions within 30 min. Besides a great number of bromoarenes, various less expensive and inactive (hetero)aryl chlorides were coupled successfully with the alkyl- and arylzinc reagents, in which active functional groups (such as -NH2) were well tolerated even in one-pot dicoupling transformations without protection. In addition, in the case of coupling with secondary alkylzinc reagents, undesired β-hydride elimination leading to isomerized linear products was efficaciously suppressed. The catalyst system also displayed superiority in the construction of heterobiaryls through the coupling of heteroarylzinc reagents and heterocylic chloroarenes which were hardly accessible from the corresponding organoboron reagents by Suzuki-coupling reactions. Therefore, the protocol described in this paper represents a mild, general, and scalable approach to access various structurally intriguing and functionalized (hetero)aryls.

Robust acenaphthoimidazolylidene palladium complexes: Highly efficient catalysts for suzuki-miyaura couplings with sterically hindered substrates

Robust acenaphthoimidazolylidene palladium complexes have been demonstrated as highly efficient and general catalysts for the sterically hindered Suzuki-Miyaura cross-coupling reactions in excellent yields even with low catalyst loadings under mild reaction conditions. The high catalytic activity of these complexes highlights that, besides the "flexible steric bulky" concept, σ-donor properties of the NHC ligands are also crucial to accelerate the transformations.

Synthesis and coordination compounds of a bis(imino)acenaphthene (BIAN)-supported N-heterocyclic carbene

The bis(imino)acenaphthene-supported N-heterocyclic carbene IPr(BIAN) has been prepared by deprotonation of the precursor imidazolium chloride. Treatment of IPr(BIAN) imidazolium chloride with Ag2O afforded the silver complex [IPr(BIAN)]AgCl which can be converted into the corresponding gold complex [IPr(BIAN)]AuCl by reaction with (tht)AuCl (tht = tetrahydrothiophene). The iridium complex [IPr(BIAN)]Ir(COD)Cl was prepared by reaction of the imidazolium chloride with KOtBu and [Ir(COD)Cl]2 and subsequently converted to the carbonyl complex [IPr(BIAN)]Ir(CO)2Cl by exposure to an atmosphere of CO. All new compounds were characterized by single-crystal X-ray diffraction, multinuclear NMR, MS and HRMS data.