605-04-9

Upstream product

• 91-22-5 quinoline 
• 2684-02-8 benzenediazonium 
• 100-34-5 benzene diazonium chloride 
• 94-36-0 dibenzoyl peroxide 
• 90-41-5 2-phenylaniline 
• 56-81-5 glycerol 
• 69956-10-1 8-phenyl-2,3,4,4a,5,6,7,8-octahydro-quinoline 
• 7664-93-9 sulfuric acid 
• 127-68-4 sodium 3-nitrobenzenesulfonate 
• 148-24-3 8-quinolinol 
• 108-86-1 bromobenzene 
• 611-33-6 8-chloroquinoline 
• 100-59-4 phenylmagnesium chloride 
• 10522-42-6 toluene-4-sulfonic acid quinolin-8-yl ester 

Downstream Products

• 110435-97-7 3-benzyl-8-phenyl-quinoline 
• 110664-06-7 3-benzyl-8-phenyl-1,2,3,4-tetrahydro-quinoline 
• 132347-10-5 1-methyl-8-phenyl-quinolinium; iodide 
• 49832-67-9 8-phenyl-[2]quinolylamine 
• 60640-18-8 8-phenyl-1,2,3,4-tetrahydro-quinoline 
• 49832-69-1 8-phenyl-2-(1H)-quinolinone 
• 24223-13-0 1-benzoyl-8-phenyl-1,2,3,4-tetrahydro-quinoline 

Relevant academic research and scientific papers

Palladium-catalyzed aryl group transfer from triarylphosphines to arylboronic acids

A study of Pd-catalyzed arylation of arylboronic acids with triarylphosphines is presented. Various parameters of this transformation, such as the oxygen presence, choice of solvent, temperature, palladium source, bases and oxidants, were tested and the optimal conditions of the aryl transfer were determined. The effect of electron-withdrawing and electron-donating substituents on the aryl groups of both reactants was also investigated. The unusual transfer of the acetate group from Pd(OAc)2 to p-nitrophenylboronic acid in the presence of PAr3 is reported. A plausible mechanism of the Pd-catalyzed aryl group transfer from PAr3 to the arylboronic acid is proposed.

Iridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines

We report a convenient method for the highly site-selective borylation of 8-arylquinoline. The reaction proceeds smoothly in the presence of a catalytic amount of [Ir(OMe)(cod)] 2and 2-phenylpyridine derived ligand using bis(pinacolato)diborane as the borylating agent. The reactions occur with high selectivity with many functional groups, providing a series of borylated 8-aryl quinolines with good to excellent yield and excellent selectivity. The borylated compounds formed in this method can be transformed into various important synthons by using known transformations.

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Rh(III)-catalyzed C8 arylation of quinoline N-oxides with arylboronic acids

Herein, we report the first RhIII-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners. This procedure is simple, and the reaction shows perfect regioselectivity, a broad substrate scope, and isolated yields of up to 92percent. We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide.

A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls

A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described. The tandem reaction proceeds efficiently at room temperature, and various biaryls and biaryl fluorosulfates were obtained in good to excellent yields. Furthermore, biaryl fluorosulfates were utilized as versatile building blocks for the preparation of terphenyls. The Royal Society of Chemistry 2020.

One-pot Negishi cross-coupling reaction of aryldiazonium salts via Ni catalysis induced by visible-light

Visible-light induced catalysis is of high interest for its mild and environmentally benign properties. Herein, a general Ni catalysis accelerated by visible-light was successfully developed for one-pot Negishi coupling reactions at room temperature in a short reaction time (2Zn generated in situ from Grignard reagents and ZnBr2. This protocol provides a convenient access to C–C bond formation for important biaryl components. It tolerates various functional groups, and Hammett study illuminates the possiblility of Ni(III)/Ni(I) redox catalytic cycle.

Cobalt-Catalyzed Suzuki Biaryl Coupling of Aryl Halides

Readily accessed cobalt pre-catalysts with N-heterocyclic carbene ligands catalyze the Suzuki cross-coupling of aryl chlorides and bromides with alkyllithium-activated arylboronic pinacolate esters. Preliminary mechanistic studies indicate that the cobalt

Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides

An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.

From Anilines to Quinolines: Iodide- and Silver-Mediated Aerobic Double C?H Oxidative Annulation–Aromatization

Quinoline synthesis from easily accessible raw materials such as anilines is a valuable and meaningful task. Herein, we communicate an iodide- and silver-mediated C?H/C?H oxidative annulation–aromatization between anilines and allyl alcohols. This protocol provides a direct route to the synthesis of quinoline derivatives from inexpensive commodities. Various kinds of anilines, even heterocyclic anilines, were shown to be workable substrates, generating the corresponding multi-substituted quinolines in good yields.

Preparation method for biaryl compound

The invention provides a preparation method for a biaryl compound. The preparation method comprises the step of performing cross coupling reaction on a substrate A and an organic zinc reagent B under a catalytic effect of a catalyst, thereby acquiring the biaryl compound, wherein a chemical structure of the substrate A is shown in the description; the organic zinc reagent B has the chemical structure shown in the description; and the catalyst is one or more of nickel salt, copper salt and cobalt salt. Compared with the other noble metal catalysts, such as, metal palladium catalyst, the catalyst adopting nickel salt, copper salt or cobalt salt is low in cost, so that the reaction cost of the biaryl compound is greatly reduced. Meanwhile, the aryl sulphonate or aryl halide shown as the substrate A has an excellent electrophilic property, is an electrophilic reagent with an excellent property and has the advantages of easiness in preparation, low cost, high activity and high stability. The substrate A and the organic zinc reagent B have cross coupling reaction under the effect of nickel salt, copper salt or cobalt salt so as to generate the biaryl compound and the reaction yield is higher.