194873-98-8

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 1423-26-3 (meta-(trifluoromethyl)phenyl)boronic acid 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 696-62-8 para-iodoanisole 
• 192887-50-6 (4-methoxyphenyl)manganese(II) chloride 
• 131086-40-3 3-(trifluoromethyl)phenyl 4-methylbenzenesulfonate 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 98-15-7 3-chlorotrifluoromethylbenzene 
• 98-08-8 α,α,α-trifluorotoluene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 401-81-0 m-trifluoromethylphenyl iodide 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 21130-91-6 triethoxy(4-methoxyphenyl)silane 
• 2251-65-2 3-(Trifluoromethyl)benzoyl chloride 

Downstream Products

• 191724-12-6 3'-(trifluoromethyl)[1,1'-biphenyl]-4-ol 

Relevant academic research and scientific papers

An easily prepared, air and moisture stable, resin-bound palladium catalyst for Suzuki cross-coupling reactions

An air and moisture stable polymer supported palladium catalyst easily prepared from a commercial available thiourea resin Deloxan THP was found to enable Suzuki cross-coupling reactions to be carried out in high yields and convenient manner.

Biaryl Synthesis from Two Different Aryl Halides with Tri(2-furyl)germane

(Matrix Presented) The coupling reaction of germanium compounds with aryl halides has been developed. The Pd(0)-catalyzed reaction of aryl halides with tri(2-furyl)germane provides aryltri(2-furyl)germanes in good yield. The cross-coupling reaction of aryltri(2-furyl)germanes with aryl halides is acheived. This allows facile synthesis of unsymmetrical biaryls from two different aryl halides.

A Highly Active Cobalt Catalyst System for Kumada Biaryl Cross-Coupling

A highly active cobalt catalyst system has been developed for the cross-coupling reactions of arylmagnesium reagents and aryl bromides. In the presence of 1 mol% CoCl 2, 2 mol% IPr·HCl and 2 mol% NaO t Bu, a wide range of (hetero)biaryls are prepared in 51-99% yields at room temperature within a short reaction time.

Nickel(II)/N-Heterocyclic Carbene Catalyzed Desulfinylative Arylation by C?S Cleavage of Aryl Sulfoxides with Phenylboronic Acids

Suzuki-Miyaura coupling of haloarenes is the most widely used protocol for the synthesis of biphenyls. Organosulfur compounds are promising electrophiles since they are abundant in nature and versatile in organic synthesis. We report here the desulfinylative Suzuki-Miyaura coupling of aryl sulfoxides with phenylboronic acids using bench-stable nickel/5-(2,4,6-triisopropylphenyl)imidazolylidene[1,5-a]pyridines as the catalyst. The ligands are readily prepared from common commercial chemicals. The method is applicable to both symmetric and unsymmetric aryl sulfoxides, and a range of biphenyls bearing various functional groups were obtained in up to 94% yield. (Figure presented.).

Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides

Herein, we report a catalyst system for Pd-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of aroyl chlorides with boronic acids to furnish biaryls. This strategy is suitable for a broad range of common aroyl chlorides and boronic acids. The synthetic utility is highlighted in the direct late-stage functionalization of pharmaceuticals and natural products capitalizing on the presence of carboxylic acid moiety. Extensive mechanistic and DFT studies provide key insight into the reaction mechanism and high decarbonylative cross-coupling selectivity.

Metal-Free Aryl Cross-Coupling Directed by Traceless Linkers

The metal-free, highly selective synthesis of biaryls poses a major challenge in organic synthesis. The scope and mechanism of a promising new approach to (hetero)biaryls by the photochemical fusion of aryl substituents tethered to a traceless sulfonamide linker (photosplicing) are reported. Interrogating photosplicing with varying reaction conditions and comparison of diverse synthetic probes (40 examples, including a suite of heterocycles) showed that the reaction has a surprisingly broad scope and involves neither metals nor radicals. Quantum chemical calculations revealed that the C?C bond is formed by an intramolecular photochemical process that involves an excited singlet state and traversal of a five-membered transition state, and thus consistent ipso–ipso coupling results. These results demonstrate that photosplicing is a unique aryl cross-coupling method in the excited state that can be applied to synthesize a broad range of biaryls.

Organic transformations catalyzed by palladium nanoparticles on carbon nanomaterials

Abstract: An efficient C–C bond coupling reactions (Suzuki–Miyaura and Glaser) catalyzed by PdO/GO nano-catalyst is presented. In addition, PdO/MWCNT nano-catalyst-mediated domino one-pot synthesis of 2-alkyl/2-aryl benzofurans has been accomplished from 2-iodophenols and terminal alkynes. The formation of benzofurans proceeds through intermolecular Sonogashira reaction followed by intramolecular nucleophilic addition of internal hydroxyl group onto the acetylenic bond. The catalyst PdO/GO has been reused successfully, with nearly no loss of activity up to 5 cycles. Graphical Abstract: : Synopsis: An efficient PdO/GO and PdO/MWCNT nanocatalysts have been developed for C–C coupling reactions like Suzuki and Glaser coupling reactions, multi-catalytic one-pot synthesis of 2-aryl, 2-alkyl benzofurans staring from 2-iodophenols and terminal alkynes. The protocol involves formation of benzofuran derivatives, i.e., Sonogashira reaction followed by 2-ethynyl phenol cyclization. [Figure not available: see fulltext.]

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

Suzuki-Miyaura cross-coupling reaction of aryl chlorides with aryl boronic acids catalyzed by a palladium dichloride adduct of N-diphenylphosphanyl-2-aminopyridine

One palladium dichloride adduct of a phosphine-pyridine ligand N-diphenylphosphanyl-2-aminopyridine (L1) [(L1)PdCl2] (1) has been prepared and structurally characterized. Compound 1 can be used as an effective catalyst for the Suzuki-Miyaura cross-coupling reactions of unreactive aryl chlorides with aryl boronic acids, and worked much better than its mono- or bidentate phosphine ligands. The reactions with a wide scope of substrates proceeded to give desired products in good to excellent yields.

An immobilized symmetrical bis-(NHC) palladium complex as a highly efficient and recyclable Suzuki-Miyaura catalyst in aerobic aqueous media

A bis-N-heterocyclic carbene (NHC) functionalized with chloropropyltriethoxysilane over silica was used to synthesize a well-defined immobilized palladium complex. This complex is a suitable and easily retrievable catalyst for Suzuki-Miyaura cross-coupling reactions under mild aqueous conditions. Excellent yields and conversions were obtained with low palladium loadings (down to 0.03 mol% Pd). The catalyst can be reused up to six cycles without the loss of its activity. The catalytic role of the NHC complex of palladium during coupling between bromobenzene and phenylboronic acid was investigated theoretically. The oxidative addition step is predicted to be endothermic in agreement with the experimental conditions.