34987-64-9

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 100-47-0 benzonitrile 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 33511-27-2 rac-N-((1S,2R)-2-hydroxy-1,2-diphenylethyl)benzamide 
• 98-80-6 phenylboronic acid 
• 55150-54-4 1-chloro-3-phenylisoquinoline 
• 4809-08-9 3-phenyl-isocoumarin 
• 100-58-3 phenylmagnesium bromide 
• 53067-91-7 2-(2-benzoylphenyl)-1-phenylethan-1-one 
• 574-66-3 Benzophenone oxime 
• 536-74-3 phenylacetylene 
• 1013-88-3 Benzophenone imine 
• 100-42-5 styrene 
• 3759-28-2 (2-cyanophenyl)acetonitrile 

Relevant academic research and scientific papers

Highly Luminescent Pincer Gold(III) Aryl Emitters: Thermally Activated Delayed Fluorescence and Solution-Processed OLEDs

Herein are described the synthesis, photophysical properties and applications of a series of luminescent cyclometalated AuIII complexes having an auxiliary aryl ligand. These complexes show photoluminescence with emission quantum yields of up to 0.79 in solution and 0.84 in thin films (4 wt % in PMMA) at room temperature, both of which are the highest reported values among AuIII complexes. Thermally activated delayed fluorescence (TADF) is the emission origin for some of these complexes. Solution-processed OLEDs made with these complexes showed sky-blue to green electroluminescence with external quantum efficiencies (EQEs) of up to 23.8 %, current efficiencies of up to 70.4 cd A?1, and roll-off of down to 1 %, highlighting the bright prospect of AuIII-TADF emitters in OLEDs.

Novel transformation of aryl 2-iodophenyl ketones into 1,3-diarylisoquinolines with (TMS)2NH, styrenes, NIS, and tBuOK

Treatment of aryl 2-iodophenyl ketones with TMS2NH in the presence of Sc(OTf)3 at warming conditions, followed by the reaction with styrenes and NIS gave N-(1-aryl-2-iodoethyl) aryl 2-iodophenyl ketimines. Further treatment of N-(1-aryl-2-iodoethyl) aryl 2-iodophenyl ketimines with tBuOK in the presence of 1,10-phenanthroline at 120 °C generated 1,3-diarylisoquinolines in moderate yields through SET from tBuOK onto the iodophenyl group to form aryl radicals, their 6-endo-trig cyclization onto the vinyl groups, and aromatization of the cyclized intermediates. The present method is a novel approach for the preparation of the isoquinoline core via two steps from aryl 2-iodophenyl ketones.

Synthesis of Isoquinoline Derivatives via Palladium-Catalyzed C?H/C?N Bond Activation of N-Acyl Hydrazones with α-Substituted Vinyl Azides

A palladium-catalyzed cyclization of N-acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α-substituted vinyl azide serves as an internal nitrogen source. Also, C?H bond activation and C?N bond cleavage have been realized using hydrazone as directing group. (Figure presented.).

Manganese-Catalyzed Carbonylative Annulations for Redox-Neutral Late-Stage Diversification

An inexpensive, nontoxic manganese catalyst enabled unprecedented redox-neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious-metal catalysts. The outstanding versatility o

Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids

A palladium-catalyzed tandem reaction of 2-(cyanomethyl)benzonitriles or 2-(2-carbonylphenyl)acetonitriles with arylboronic acids in water has been developed for the first time. This reaction features good functional group tolerance and provides a new strategy for the synthesis of diverse isoquinolines under mild conditions. The use of water as the reaction medium makes the synthesis process environmentally benign. Preliminary mechanistic experiments indicate that the major reaction pathway involves carbopalladation of the C(sp3)-cyano group and subsequent intramolecular cyclization findings that were further supported by density functional theory (DFT) calculations.

N-O Bond as External Oxidant in Group 9 Cp?M(III)-Catalyzed Oxidative C-H Coupling Reactions

Group 9 Cp?M(III) (M = Co, Rh, Ir) complexes have been extensively investigated as catalysts in a variety of C-H activation reactions. Typically, late metal-based silver or copper salt was used (while needed) as oxidant in these catalytic systems. Herein, we report our discovery of a potentially general type of N-O bond-containing oxidants, which allowed the mild and efficient syntheses of isocoumarins, isoquinolines, isoquinolinone, and styrenes via C-H activation catalyzed by group 9 Cp?M(III) complexes. By using Cp?Rh(III)-catalyzed isocoumarin synthesis as a model reaction, experimental and theoretical mechanistic studies were conducted. The results concluded that the Rh(III)-Rh(I)-Rh(III) rather than the Rh(III)-Rh(V)-Rh(III) pathway is more likely involved in the mechanism, and both the C-H activation and oxidation of the Cp?Rh(I) species were involved in the turnover-limiting step.

Palladium-Catalyzed C-H Functionalization of Aromatic Oximes: A Strategy for the Synthesis of Isoquinolines

An efficient strategy for synthesis of isoquinolines via Pd(II)-catalyzed cyclization reaction of oximes with vinyl azides or homocoupling of oximes is reported. Oximes could serve as a directing group and an internal oxidant in the transformation. This reaction features good functional group tolerance and provides a useful protocol for the synthesis of different kinds of isoquinolines under mild conditions. Some control experiments and 15N isotope labeling experiments were conducted for the mechanistic research. (Chemical Equation Presented).

(Pentamethylcyclopentadienyl)cobalt(III)-Catalyzed Oxidative [4+2] Annulation of N H Imines with Alkynes: Straightforward Synthesis of Multisubstituted Isoquinolines

A synthetic method for isoquinoline synthesis via a [4+2] annulation of N H imines with alkynes using the high-valent (pentamethylcyclopentadienyl)cobalt(III) [Cp*Co(III)] catalyst is described. Cerium(IV) sulfate was found to be an efficient oxidant in lieu of the commonly used copper or silver salts. Broad substrate scope, high functional group tolerance, and generally good yields were observed. (Figure presented.).

Gold-Catalyzed Ammonium Acetate Assisted Cascade Cyclization of 2-Alkynylarylketones

An ammonium acetate assisted gold-catalyzed cascade cyclization reaction of 2-alkynylarylketones is described. Under the reported conditions, a gold-catalyzed intramolecular cyclization of 2-alkynylarylketones takes place through two competing reaction mechanisms?-?a 5-exo-dig or a 6-endo-dig cyclization-leading to two regioisomeric intermediates: isobenzofuranium or isobenzopyrylium. In the presence of ammonium acetate, the two intermediate compounds undergo further rearrangement to 2,3-disubstituted indenones and 1,3-disubstituted isoquinolines, respectively. While both reaction pathways proceed via a cyclization-rearrangement cascade, the gold-mediated 5-exo-dig process is especially notable, as it provides a novel cyclization protocol of 2-alkynylarylketones.

Enhancing effects of salt formation on catalytic activity and enantioselectivity for asymmetric hydrogenation of isoquinolinium salts by dinuclear halide-bridged iridium complexes bearing chiral diphosphine ligands

Asymmetric hydrogenation of 1- and 3-substituted and 1,3-disubstituted isoquinolinium chlorides using triply halide-bridged dinuclear iridium complexes [{Ir(H)(diphosphine)} 2(μ -Cl)3]Cl has been achieved by the strategy of HCl salt formation of isoquinolines to afford the corresponding chiral 1,2,3,4-tetrahydroisoquinolines (THIQs) in high yields and with excellent enantioselectivities after simple basic workup. The effects of salt formation have been investigated by time-course experiments, which revealed that the generation of isoquinolinium chlorides clearly prevented formation of the catalytically inactive dinuclear trihydride complex, which was readily generated in the catalytic reduction of salt-free isoquinoline substrates. Based on mechanistic investigations, including by 1H and 31P{1H} NMR studies and the isolation and characterization of several intermediates, the function of the chloride anion of the isoquinolinium chlorides has been elucidated, allowing us to propose a new outer-sphere mechanism involving coordination of the chloride anion of the substrates to an iridium dihydride species along with a hydrogen bond between the chloride ligand and the N-H proton of the substrate salt.