93472-52-7

Upstream product

• 1138735-04-2 1-(1-azidopropyl)-2-(phenylethynyl)benzene 
• 690229-61-9 2-(2-propionylphenyl)acetonitrile 
• 98-80-6 phenylboronic acid 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 2890-85-9 N-acetyl-1-phenylpropenamine 
• 16717-64-9 1-azidostyrene 
• 536-74-3 phenylacetylene 
• 2157-50-8 propiophenone oxime 
• 100-42-5 styrene 
• 23517-38-6 propiophenone oxime 
• 93-55-0 1-phenyl-propan-1-one 
• 98-86-2 acetophenone 
• 156605-56-0 1-phenylethan-1-one O-pivaloyl oxime 

Relevant academic research and scientific papers

Rhodium(iii)-catalyzed annulation of enamides with sulfoxonium ylides toward isoquinolines

An efficient rhodium(iii)-catalyzed C-H activation followed by intermolecular annulation between enamides and sulfoxonium ylides has been developed. The transformation proceeds smoothly with a broad range of substrates, affording a series of isoquinoline derivatives in moderate to good yields under additive-free conditions.

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.

Bidentate Directing-Enabled, Traceless Heterocycle Synthesis: Cobalt-Catalyzed Access to Isoquinolines

Traceless heterocycle synthesis based on transition-metal-catalyzed C-H functionalization is synthetically appealing but has been realized only in monodentate directing systems. Bidentate directing systems allow for the achievement of high catalytic reactivity without the need for a high-cost privileged ligand. The first bidentate directing-enabled, traceless heterocycle synthesis is demonstrated in the cobalt-catalyzed synthesis of isoquinolines via 2-hydrazinylpyridine-directed C-H coupling/cyclization with alkynes. Convenient directing group installation through a ubiquitously present ketone group allows synthetic elaboration for complex molecules.

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).

Methyl ketone oxime esters as nucleophilic coupling partners in Pd-catalyzed C-H alkylation and application in the synthesis of isoquinolines

Methyl ketone oxime esters have been found to be excellent coupling partners for C(sp2)-C(sp3) bond formation via Pd-catalyzed aromatic C-H activation. This transformation forms the basis of an approach to regioselectively synthesize substituted isoquinolines via coupling with aryloxime esters. Our mechanistic studies suggested that the reaction proceeded through Pd(II)-catalyzed aromatic C-H activation, tautomerization, and a 1,3-shift of the palladacycle-ligated methyl ketone oxime ester to enable the C-C bond formation by reductive elimination, and intramolecular condensation of an imido-Pd(II) intermediate to form the heterocycle. The aryloxime group not only was used as a directing group for Pd-catalyzed aromatic C-H activation but also functioned as an internal oxidant to allow the reaction to be redox-neutral. Our study illuminated the scope and limitations of this C-H alkylation process, which may serve as the point of departure for developing other C-H functionalization reactions using oxime esters and potentially other carbonyl derivatives as the nucleophilic coupling partners.

Coupling of enamides with alkynes or arynes for synthesis of substituted pyridines and isoquinolines via amide activation

A novel and general procedure for Cu-catalyzed coupling of enamides with alkynes to synthesize substituted pyridines was developed. The chemistry was allowed to extend to the synthesis of substituted isoquinolines by coupling of enamides with arynes under transition-metal-free conditions.

ISOQUINOLINE DERIVATIVES FROM THE RITTER-TYPE REACTION OF VINYL CATIONS

Both silver-assisted reaction of β-arylvinyl bromides and the photolysis in nitriles gave isoquinoline derivatives, indicating that the Ritter reaction involving a vinyl cation took place.