70125-61-0

Upstream product

• 119-65-3 isoquinoline 
• 23586-54-1 phenylthalium(III) di(trifluoroacetate) 
• 62882-02-4 6-chloroisoquinoline 
• 368-47-8 phenyltrifluorosilane 
• 98-13-5 Phenyltrichlorosilane 
• 100-59-4 phenylmagnesium chloride 
• 34784-05-9 6-bromo-isoquinoline 
• 98-80-6 phenylboronic acid 
• 675576-26-8 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline 
• 100-58-3 phenylmagnesium bromide 
• 3218-36-8 4-Phenylbenzaldehyde 
• 22483-09-6 2,2-dimethoxyethylamine 

Downstream Products

• 24464-39-9 6-phenyl-1,2,3,4-tetrahydro-isoquinoline 

Relevant academic research and scientific papers

Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles

A nickel/dppf catalyst system was found to successfully achieve the Suzuki-Miyaura cross-coupling reactions of 3- and 4-chloropyridine and of 6-chloroquinoline but not of 2-chloropyridine or of other α-halo-N-heterocycles. Further investigations revealed that chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation of stable dimeric nickel species that are catalytically inactive in Suzuki-Miyaura cross-coupling reactions. However, the corresponding Kumada-Tamao-Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of Grignard reagents.

Iridium(III)-Catalyzed C(3)-H Alkylation of Isoquinolines via Metal Carbene Migratory Insertion

An Ir(III)-catalyzed C(3)-H alkylation of N-acetyl-1,2-dihydroisoquinolines with diverse acceptor-acceptor diazo compounds has been achieved under a single catalytic system via metal carbene migratory insertion. Moreover, further synthetic transformations of the alkylated products such as aromatization, selective decarboxylation, and decarbonylation lead to the formation of several synthetically viable isoquinoline derivatives having immense potentials.

Utilization of Borane-Catalyzed Hydrosilylation as a Dearomatizing Tool: Six-Membered Cyclic Amidine Synthesis from Isoquinolines and Pyridines

In this study, a convenient strategy to synthesize six-membered?? cyclic amidines from isoquinolines and pyridines has been developed. Borane-catalyzed hydrosilylation of each N-heteroarene was utilized as a dearomatizing tool. Substrate scope is broad with respect to both isoquinolines and pyridines, with various reaction pathways depending on the substitution pattern of the N-heteroarenes. The reaction mechanism and reactivity of each class of N-heteroarenes has been discussed. The resulting six-membered (Z)-sulfonyl amidine products are rarely reported and are mostly unprecedented. The scalability of this method and versatility of the cyclic amidine products are also presented.

Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons

We herein describe a chiral diboron-templated highly diastereoselective and enantioselective reductive coupling of isoquinolines that provided expedited access to a series of chiral substituted bisisoquinolines in good yields and excellent ee's under mild conditions. The method enjoys a broad substrate scope and good functional group compatibility. Mechanistic investigation suggests the reaction proceeds through a concerted [3,3]-sigmatropic rearrangement.

Synthesis and utility of dihydropyridine boronic esters

When activated by an acylating agent, pyridine boronic esters react with organometallic reagents to form a dihydropyridine boronic ester. This intermediate allows access to a number of valuable substituted pyridine, dihydropyridine, and piperidine products.

Palladium-catalyzed Hiyama cross-coupling of aryltrifluorosilanes with aryl and heteroaryl chlorides

An efficient, palladium-catalyzed Hiyama cross-coupling reaction of aryltrifluorosilanes with aryl chlorides has been developed. A wide variety of functionalized biaryl derivatives were isolated in good to excellent yields. The scope of this reaction has also been extended to heteroaryl chlorides, affording the corresponding heterobiaryl compounds in high yields.

Nonlinear optical chromophores with isoquinolines, thieno[2,3-c]-pyridines and 2-(2′-thienyl)pyridines as inherently polarized π-electron bridges

The synthesis and first hyperpolarizabilities of a series of isoquinolines and isoquinolinium salts, and also thienopyridines, thienylpyridines, and the corresponding pyridinium salts, determined by hyper-Rayleigh scattering in solution at 1064 and 1300 nm, are reported. These chromophores exhibit markedly high β values. Some of them show absorption maxima well below 400 nm, enabling their use in blue transparent frequency doubling devices. We have performed X-ray structure analyses for thienopyridines 13a,c.

The Free-Radical Phenylation of Isoquinolinium Cation

Free radical phenylation of isoquinolinium cation has been effected by photolysis of phenylthallium(III)di(trifluoroacetate) in a trifluoroacetic acid solution of isoquinoline.Analysis (g.l.c. and h.p.l.c.) of the isomeric phenylisoquinoline mixture showed that the dominant product (81.1percent) was 1-phenylisoquinoline, in accordance with two published theoretical predictions

Versatile and Efficient Synthesis of Aryl-1,2,3,4-tetrahydroisoquinolines: Nickel(II) Phosphine Ligand Catalyzed Coupling of Arylmagnesium Halides to Haloisoquinolines

Dichloronickel(II) (dppp) was used as catalyst to prepare some previously unreported arylisoquinolines 3, which were in turn hydrogenated to aryl-1,2,3,4-tetrahydroisoquinolines 2.This procedure is the most direct and ef