2876-44-0

Upstream product

• 17666-89-6 1-[2]naphthyl-octan-1-one 
• 111-66-0 oct-1-ene 
• 3857-83-8 2-naphthyl triflate 
• 30089-00-0 9-octyl-9-bora-bicyclo[3.3.1]nonane 
• 91-20-3 naphthalene 
• 111-64-8 n-octanoic acid chloride 
• 629-27-6 1-Iodooctane 
• 32316-92-0 naphthalene-2-boronic acid 
• 1041479-71-3 C₂₄H₅₁In 
• 612-55-5 2-iodonaphthalene 
• 93-04-9 2-Methoxynaphthalene 
• 1070-00-4 trioctylaluminum 
• 1503-86-2 2-naphthyl pivalate 
• 16519-26-9 diethyl naphthalen-2-yl phosphate 

Relevant academic research and scientific papers

Nickel-Catalyzed Csp2-Csp3 Cross-Coupling via C-O Bond Activation

A new and efficient nickel-catalyzed alkylation of CAr-O electrophiles with B-alkyl-9-BBNs is described. The transformation is characterized by its functional group tolerance and provides a practical and versatile access to various Csp2/s

A Ball-Milling-Enabled Cross-Electrophile Coupling

The nickel-catalyzed cross-electrophile coupling of aryl halides and alkyl halides enabled by ball-milling is herein described. Under a mechanochemical manifold, the reductive C-C bond formation was achieved in the absence of bulk solvent and air/moisture sensitive setups, in reaction times of 2 h. The mechanical action provided by ball milling permits the use of a range of zinc sources to turnover the nickel catalytic cycle, enabling the synthesis of 28 cross-electrophile coupled products.

C-F activation for C(sp2)-C(sp3) cross-coupling by a secondary phosphine oxide (SPO)-nickel complex

A secondary phosphine oxide (SPO)-nickel catalyst allowed the activation of otherwise inert C-F bonds of unactivated arenes in terms of challenging couplings with primary and secondary alkyl Grignard reagents. The C-F activation is characterized by mild reaction conditions and high levels of branched selectivity. Electron-rich and electron-deficient arenes were suitable electrophiles for this transformation. In addition, this strategy also proved suitable to heterocycles and for the activation of C-O bonds under slightly modified conditions.

Nickel-catalyzed cross-coupling of aryl or 2-menaphthyl quaternary ammonium triflates with organoaluminum reagents

The cross-coupling of aryltrimethylammonium triflates with AlMe3 and β-H-containing trialkylaluminums was performed in dioxane at 110 °C under catalysis of (dppp)NiCl2 to afford alkylated arenes. The cross-coupling of 2-menaphthyltri

Ionic iron(III) complexes bearing a dialkylbenzimidazolium cation: Efficient catalysts for magnesium-mediated cross-couplings of aryl phosphates with alkyl bromides

A series of ionic iron(III) complexes of general formula [HLn][FeX4] (HL1?=?1,3-dibenzylbenzimidazolium cation, X?=?Cl, 1; HL1, X?=?Br, 2; HL2?=?1,3-dibutylbenzimidazolium cation, X?=?Br, 3; HL3?=?1,3-bis(diphenylmethyl)benzimidazolium cation, X?=?Br, 4) were easily prepared in high yields by the direct reaction of FeX3 with 1 equiv. of [HLn]X under mild conditions. All of them were characterized using elemental analysis, Raman spectroscopy and electrospray ionization mass spectrometry, and X-ray crystallography for 1 and 4. In the presence of magnesium turnings and LiCl, these air- and moisture-insensitive complexes showed high catalytic activities in direct cross-couplings of aryl phosphates with primary and secondary alkyl bromides with broad substrate scope, wherein complex 4 was the most effective.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides

A nickel-catalyzed cross-electrophile coupling of aryl triflates and nonaflates with alkyl iodides using manganese(0) as a reductant is described. The method is applicable to the reductive alkylation of various aryl sulfonates, including o -borylaryl triflate, which enabled efficient construction of diverse alkylated arenes under mild conditions.

Alkyl Grignard cross-coupling of aryl phosphates catalyzed by new, highly active ionic iron(II) complexes containing a phosphine ligand and an imidazolium cation

A novel family of ionic iron(ii) complexes of the general formula [HL][Fe(PR′3)X3] (HL = 1,3-bis(2,6-diisopropylphenyl)imidazolium cation, HIPr, R′ = Ph, X = Cl, 2; HL = HIPr, R′ = Cy, X = Cl, 3; HL = HIPr, R′ = Ph, X = Br, 4; HL = HIPr, R′ = Cy, X = Br, 5; HL = 1,3-bis(2,4,6-trimethylphenyl)imidazolium cation, HIMes, R′ = Cy, X = Br, 6) was easily prepared via a stepwise approach in 88%-92% yields. In addition, an ionic iron(ii) complex, [HIPr][Fe(C4H8O)Cl3] (1), has been isolated from the reaction of FeCl2(THF)1.5 with one equiv. of [HIPr]Cl in 90% yield and it can further react with one equiv. of PPh3 or PCy3, affording the corresponding target iron(ii) complex 2 or 3, respectively. All these complexes were characterized by elemental analysis, electrospray ionization mass spectrometry (ESI-MS), 1H NMR spectroscopy and X-ray crystallography. These air-insensitive complexes 2-6 showed high catalytic activities in the cross-coupling of aryl phosphates with primary and secondary alkyl Grignard reagents with a broad substrate scope, wherein [HIPr][Fe(PCy3)Br3] (5) was the most effective. Complex 5 also catalyzes the reductive cross-coupling of aryl phosphates with unactivated alkyl bromides in the presence of magnesium turnings and LiCl, as well as the corresponding one-pot acylation/cross-coupling sequence under mild conditions.

Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C-O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination

In the presence of trialkylaluminum reagents, diverse aryl methyl ethers can be transformed into valuable products by C-O bond-cleaving alkylation, for the first time without the limiting β-hydride elimination. This new nickel-catalyzed dealkoxylative alkylation method enables powerful orthogonal synthetic strategies for the transformation of a variety of naturally occurring and easily accessible anisole derivatives. The directing and/or activating properties of aromatic methoxy groups are utilized first, before they are replaced by alkyl chains in a subsequent coupling process.

Copper-Catalyzed Coupling of Triaryl- and Trialkylindium Reagents with Aryl Iodides and Bromides through Consecutive Transmetalations

An efficient copper(I)-catalyzed coupling of triaryl and trialkylindium reagents with aryl iodides and bromides is reported. The reaction proceeds at low catalyst loadings (2 mol %) and generally only requires 0.33 equivalents of the triorganoindium reagent with respect to the aryl halide as all three organic nucleophilic moieties of the reagent are transferred to the products through consecutive transmetalations. The reaction tolerates a variety of functional groups and sterically hindered substrates. Furthermore, preliminary mechanistic studies that entailed the synthesis and characterization of potential reaction intermediates offered a glimpse of the elementary steps that constitute the catalytic cycle.

Method for producing Suzuki coupling compound catalysed by a nickel compound

There are disclosed a method for producing a cross-coupling compound of formula (3):(Y-)(n-1)R1-R2-(R1)(n'-L) ???wherein R1 represents ???a substituted or unsubstituted, linear, branched, or cyclic hydrocarbon group, and ???n and n' each represent 1 or 2, ???provided that when n and n' are the same, both n and n' are not 2, ???R2 represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group, ???and ???Y represents R2 or X1, wherein R2 is as defined above, and X1 represents a chlorine, bromine or iodine atom, ???which method comprises reacting ???an organic halide of formula (1):n'(R1X1?n), ???wherein R1 is as defined above and carbon atoms at the α and β positions relative to X1 are sp3 carbon atoms, and X1, n and n' are as defined above, ???with a boron compound of formula (2):m{R2(BX2?2)n'}, ???wherein R2 and n' are as defined above, ???X2 independently represents a hydroxyl group or an alkoxy or aryloxy group, or X22 together form an alkoxy or aryloxy group, and m represents 1 or 2, and m≤n, and the boron atom is bonded with an sp2 carbon atom of R2 group, or a boronic acid trimer anhydride thereof, in the presence of a base and a catalyst comprising a nickel compound and a compound of formula (i): ???wherein R3 represents a substituted or unsubstituted alkyl group, ???R4 represents a hydrogen atom or a substituted or unsubstituted alkyl group, ???1 represents an integer of 1 to 3, and ???p and q each represents an integer of 0 to 2; and a catalyst.