57479-35-3

Upstream product

• 1430224-24-0 8-(trifluoromethanesulfonyl)quinoline 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1613-37-2 Quinoline N-oxide 
• 2403-50-1 2-(4-methoxyphenyl)-1,3-dioxolane 
• 16567-18-3 8-bromoquinoline 
• 916314-51-7 quinolin-8-yl methanesulfonate 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 91-22-5 quinoline 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 148-24-3 8-quinolinol 
• 10522-42-6 toluene-4-sulfonic acid quinolin-8-yl ester 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 689247-75-4 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-octane-1-sulfonic acid quinolin-8-yl ester 

Relevant academic research and scientific papers

Ru-Catalyzed Deoxygenative Regioselective C8-H Arylation of Quinoline N-Oxides

Regioselective C-H functionalization on quinolines is of high interest to lead to value-added products. Herein, we describe the development of Ru-catalyzed deoxygenative regioselective C8 arylation of quinoline N-oxides with arylboronic esters. Mechanistic studies revealed that it proceeds in a tandem process of arylation and then deoxygenation, wherein both steps were found to be catalytic with the ruthenium species.

Catalyst shuttling enabled by a thermoresponsive polymeric ligand: Facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium

A polymeric monophosphine ligand WePhos has been synthesized and complexed with palladium(ii) acetate [Pd(OAc)2] to generate a thermoresponsive pre-catalyst that can shuttle between water and organic phases, with the change being regulated by temperature. The structure of the polymeric ligand was confirmed with matrix-assisted laser desorption/ionization-time-of-flight (MALDI-TOF) mass spectrometry and size-exclusion chromatography (SEC) analysis, as well as nuclear magnetic resonance (NMR) measurements. This polymeric metal complex enables highly efficient Pd-catalyzed cross-couplings and tandem reactions using 50 to 500 ppm palladium, and this can facilitate reactions that are tolerant to a broad spectrum of (hetero)aryl substrates and functional groups, as demonstrated with 73 examples with up to 99% isolated yields. Notably, 97% Pd remained in the aqueous phase after 10 runs of catalyst recycling experiments, as determined via inductively coupled plasma-atomic emission spectrometry (ICP-AES) measurements, indicating highly efficient catalyst transfer. Furthermore, a continuous catalyst recycling approach has been successfully developed based on flow chemistry in combination with the catalyst shuttling behavior, allowing Suzuki-Miyaura couplings to be conducted at gram-scales with as little as 10 ppm Pd loading. Given the significance of transition-metal catalyzed cross-coupling and increasing interest in sustainable chemistry, this work is an important step towards the development of a responsive catalyst, in addition to having high activity, by tuning the structures of the ligands using polymer science.

Dibenzofuran and dibenzothiophene based palladium(ii)/NHC catalysts-synthesis and applications in C-C bond formation

In the quest for a new ligand system for Pd(ii)/NHCs, we developed new dibenzofuran and dibenzothiophene based palladium N-heterocyclic carbene catalysts D1-D6 in good yields. All the catalysts were characterized by multinuclear NMR spectroscopy and HRMS. The X-ray crystal structure of the representative dibenzothiophene based Pd(ii)/NHC D4 was determined. Among the precatalysts, D1 was shown to be highly effective in the Suzuki-Miyaura cross-coupling reaction of heterocyclic bromides with boronic acids. Besides, D1 affords diverse arylated benzoxazoles via direct C-H bond functionalization with substituted bromo derivatives.

Catalytic asymmetric hydrogenation of quinoline carbocycles: Unusual chemoselectivity in the hydrogenation of quinolines

The reduction of quinolines selectively took place on their carbocyclic rings to give 5,6,7,8-tetrahydroquinolines, when the hydrogenation was conducted in the presence of a Ru(η3-methallyl)2(cod)-PhTRAP catalyst. The chiral ruthenium catalyst converted 8-substituted quinolines into chiral 5,6,7,8-tetrahydroquinolines with up to 91:9 er. This journal is

Palladium-catalyzed Suzuki-Miyaura coupling of aryl sulfamates with arylboronic acids

Readily available NHC-Pd(ii)-Mp complexes 2 showed efficient catalytic activity toward the Suzuki-Miyaura coupling of aryl sulfamates with arylboronic acids or potassium phenyltrifluoroborate, giving the expected coupling products in good to high yields.

Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature

trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel(II) complex/PCy 3 system has been successfully applied as catalyst for the Suzuki-Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni(II)-based catalyst can be utilized as an alternative to Ni(COD) 2/PCy3 to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.

Ni(COD)2/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature

Reaction conditions for the Ni(COD)2/PCy3 catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)2/PCy 3 was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature. This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives. In combination with the recently developed Nicatalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible (Figure presented).

Rh(NHC)-catalyzed direct and selective arylation of quinolines at the 8-position

A new catalytic protocol for the regioselective direct arylation of quinoline derivatives at the 8-position has been developed. The reaction is catalyzed by a Rh(NHC) system, and the choice of the NHC ligand was most important for achieving high reactivit

Air-stable PinP(O)H as preligand for palladium-catalyzed Kumada couplings of unactivated tosylates

Air-stable and easily accessible PinP(O)H enables highly efficient palladium-catalyzed Kumada cross-coupling reactions of aryl tosylates. The in situ generated catalyst proved applicable not only to electron-rich and electron-poor carbocyclic tosylates but also to heterocyclic tosylates, such as pyridine and quinoline derivatives. The results described herein constitute the first use of air-stable secondary phosphine oxides as preligands for transition-metal-catalyzed coupling reactions between organometallic species and tosylates.

A highly efficient microwave-assisted Suzuki coupling reaction of aryl perfluorooctylsulfonates with boronic acids

A new strategy to improve the efficiency of Suzuki coupling reactions is introduced by combining fast microwave reaction with easy fluorous separation. Aryl perfluorooctylsulfonates derived from the corresponding phenols are coupled with aryl boronic acid