47230-38-6

Usage

InChI:InChI=1/C18H18O4/c1-3-21-17(19)15-9-5-13(6-10-15)14-7-11-16(12-8-14)18(20)22-4-2/h5-12H,3-4H2,1-2H3

Upstream product

• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 75-77-4 chloro-trimethyl-silane 
• 131379-16-3 4-(ethoxycarbonyl)phenylzinc iodide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 108-37-2 1-bromo-3-chlorobenzene 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 766-85-8 3-methoxy-1-iodobenzene 
• 529-28-2 4-iodoanisol 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 696-62-8 para-iodoanisole 
• 108-24-7 acetic anhydride 
• 572901-35-0 (Z)-2-(2,2-diisopropyl-1-oxa-2-silacyclopent-3-ylidene)acetaldehyde 

Downstream Products

• 1667-12-5 4,4'-bis(hydroxymethyl)biphenyl 
• 20248-86-6 4-4'-bis(bromomethyl)biphenyl 
• 1266348-24-6 C₃₀H₂₂O₄ 
• 1266348-25-7 (2E,2′E)-3,3′-([1,1′-biphenyl]-4,4′-diyl)bis(1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one) 
• 1266348-26-8 (2E,2′E)-3,3′-([1,1′-biphenyl]-4,4′-diyl)bis(1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one) 
• 1266348-23-5 C₃₀H₂₂O₂ 
• 56523-93-4 C₇₀H₉₀O₄ 

Relevant academic research and scientific papers

Tandem Mn–I Exchange and Homocoupling Processes Mediated by a Synergistically Operative Lithium Manganate

Pairing lithium and manganese(II) to form lithium manganate [Li2Mn(CH2SiMe3)4] enables the efficient direct Mn–I exchange of aryliodides, affording transient (aryl)lithium manganate intermediates which in turn undergo spontaneous C?C homocoupling at room temperature to furnish symmetrical (bis)aryls in good yields under mild reaction conditions. The combination of EPR with X-ray crystallographic studies has revealed the mixed Li/Mn constitution of the organometallic intermediates involved in these reactions, including the homocoupling step which had previously been thought to occur via a single-metal Mn aryl species. These studies show Li and Mn working together in a synergistic manner to facilitate both the Mn–I exchange and the C?C bond-forming steps. Both steps are carefully synchronized, with the concomitant generation of the alkyliodide ICH2SiMe3 during the Mn–I exchange being essential to the aryl homocoupling process, wherein it serves as an in situ generated oxidant.

Sustainable Synthesis of Biaryls Using Silica Supported Ferrocene Appended N-Heterocyclic Carbene-Palladium Complex

Abstract: A novel silica supported ferrocene appended N-heterocyclic carbene-palladium complex (SilFemBenzNHC@Pd) has been prepared and characterized by using fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). This novel complex served as a robust heterogeneous catalyst for the synthesis of biaryls via homocoupling of aryl boronic acids under base-free conditions in water. Recyclability experiments were executed successfully for six successive runs. Graphic Abstract: [Figure not available: see fulltext.]

Spatial anion control on palladium for mild C-H arylation of arenes

C-H arylation of arenes without the use of directing groups is a challenge, even for simple molecules, such as benzene. We describe spatial anion control as a concept for the design of catalytic sites for C-H bond activation, thereby enabling nondirected C-H arylation of arenes at ambient temperature. The mild conditions enable late-stage structural diversification of biologically relevant small molecules, and site-selectivity complementary to that obtained with other methods of arene functionalization can be achieved. These results reveal the potential of spatial anion control in transition-metal catalysis for the functionalization of C-H bonds under mild conditions.

Palladium-Catalyzed Silylation of Aryl Chlorides with Bulky Dialkoxydisilanes

Arylsilanes bearing a bulky alkoxy group on the silicon were synthesized from aryl chlorides and dialkoxydisilanes under reaction conditions utilizing SingaCycle-A3 as a palladium precatalyst and lithium benzoate in wet DMA. This report proposes the first direct and catalytic method for introducing tert -butoxy- or 1-adamantyloxysilyl groups onto various aryl moieties through the silylation reaction.

Metal-Reductant-Free Electrochemical Nickel-Catalyzed Couplings of Aryl and Alkyl Bromides in Acetonitrile

While reductive cross-electrochemical coupling is an attractive approach for the synthesis of complex molecules at both small and large scale, two barriers for large-scale applications have remained: the use of stoichiometric metal reductants and a need for amide solvents. In this communication, new conditions that address these challenges are reported. The nickel-catalyzed reductive cross-coupling of aryl bromides with alkyl bromides can be conducted in a divided electrochemical cell using acetonitrile as the solvent and diisopropylamine as the sacrificial reductant to afford coupling products in synthetically useful yields (22-80%). Additionally, the use of a combination of the ligands 4,4′,4″-tri-tert-butyl-2,2′:6′,2′-terpyridine and 4,4′-di-tert-butyl-2,2′-bipyridine is essential to achieve high yields.

One-pot two-step stannylation/Stille homocoupling of aryl bromides and iodides under solvent-free conditions

A new highly efficient solvent-free method for aryl bromide (iodide) homocoupling comprising the use of Pd(OAc)2/PCy3 system in the presence of CsF is suitable for substrates bearing functional groups not tolerant to lithium-, magnesium-, zincorganic reagents and strong bases.

Nickel-Catalyzed Electrochemical Reductive Homocouplings of Aryl and Heteroaryl Halides: A Useful Route to Symmetrical Biaryls

Due to their widespread presence in functional materials and pharmaceuticals, biaryls are of fundamental importance in organic chemistry. Methods for the synthesis of symmetrical biaryls generally involve both metallic reduction and transition-metal catalysis. In this work, we show that electroreduction can also constitute a very relevant way to achieve the nickel-catalyzed reductive synthesis of symmetrical biaryl compounds. Therefore, it is demonstrated that both aryl and heteroaryl halides undergo reductive coupling to furnish the corresponding symmetrical biaryls in fair to excellent yields. Reactions are performed under very mild conditions thus ensuring important functional group tolerance.

Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes

Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium salts.

Electrochemical Nickel Catalysis for Sp2-Sp3 Cross-Electrophile Coupling Reactions of Unactivated Alkyl Halides

A constant-current electrochemical method for reducing catalytic nickel complexes in sp2-sp3 cross-electrophile coupling reactions has been developed. The electrochemical reduction provides reliable nickel catalyst activation and turnover and offers a tunable parameter for reaction optimization, in contrast to more standard activated metal powder reductants. The electrochemical reactions give yields (i.e., 51-86%) and selectivities as high or superior to those using metal powder reductants and provide access to a wider substrate scope.

Synthesis of dendrimer-type viologen and its use in Pd-mediated homocoupling of aryl halides

Dendrimer-type viologen (V2+.D.) was prepared from mesitylene and 4.4′-bipyridyl. Electroreduction of V2+.D. gave the corresponding quinoid (V0.D.), which promoted Pd-catalyzed homocoupling of aryl bromides Ar-Br to give the corresponding biaryls Ar-Ar in moderate to good yields.