1717-22-2

Upstream product

• 100-63-0 phenylhydrazine 
• 371-40-4 4-fluoroaniline 
• 61272-76-2 4-fluoro-2-iodoaniline 
• 98-80-6 phenylboronic acid 
• 255724-71-1 5-fluoro-2-iodoaniline 
• 108-86-1 bromobenzene 
• 59-88-1 phenylhydrazine hydrochloride 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 700-36-7 2-bromo-4-fluoronitrobenzene 
• 1073-06-9 3-fluorobromobenzene 
• 591-50-4 iodobenzene 
• 1478-01-9 5-fluoro-2-nitro-1,1’-biphenyl 

Downstream Products

• 343-40-8 3-fluoro-9H-fluorene 
• 1507941-55-0 (2‐fluorophenanthridin‐6‐yl)diphenylphosphine oxide 

Relevant academic research and scientific papers

CoPc-catalyzed selective radical arylation of anilines with arylhydrazines for synthesis of 2-aminobiaryls

CoPc-catalyzed selective radical arylation of anilines with arylhydrazines to afford 2-aminobiaryls in moderate to good yields is described. This journal is the Partner Organisations 2014.

Air-promoted direct radical arylation of anilines with arylhydrazines

Air-promoted coupling reaction of arylhydrazines and arylamines is developed for the selective synthesis of 2-aminobiaryls. This protocol provides a green, cost-effective, and scale-up method for preparation of 2-aminobiaryls.

α-Bromoacrylic Acids as C1 Insertion Units for Palladium-Catalyzed Decarboxylative Synthesis of Diverse Dibenzofulvenes

Herein α-bromoacrylic acids have been employed as C1 insertion units to achieve the palladium-catalyzed [4 + 1] annulation of 2-iodobiphenyls, which provides an efficient platform for the construction of diverse dibenzofulvenes. This protocol enables the formation of double C(aryl)-C(vinyl) bonds via a C(vinyl)-Br bond cleavage and decarboxylation. It is particularly noteworthy that the method features a broad substrate scope, and various interesting frameworks, such as bridged ring, fused (hetero)aromatic ring, and divinylbenzene, can be successfully incorporated into the products.

Catalytic enantioselective synthesis of chiral spirocyclic 1,3-diketones: Via organo-cation catalysis

An SPA-triazolium bromide-catalyzed transannular C-acylation of enol lactones is presented. This methodology provides convenient access to a range of enantioenriched spirocyclic 1,3-diketones in moderate to high yields and enantioselectivities and features a broad substrate scope in terms of enol lactones. The catalytic capability of this triazolium salt catalyst is also demonstrated in this enantioselective transformation, which could inspire its further application. This journal is

Asymmetric palladium complex, preparation method and application thereof in catalysis of olefin polymerization

The invention belongs to the technical field of chemical synthesis, and particularly relates to an asymmetric palladium complex, a preparation method and application thereof in catalysis of olefin polymerization. According to the asymmetric alpha-diimine palladium complex disclosed by the invention, a rigid camphanyl skeleton with large steric hindrance is adopted, so that the axial steric hindrance effect of a catalyst can be improved, and the thermal stability and polymerization activity of the catalyst are further improved; aniline with only one phenyl substituted ortho-position is adopted, and the other ortho-position (6-position) has no substituent, so that the coordination of olefin substituted by large steric hindrance is facilitated, and the catalytic activity is improved; in addition, the complex is simple to synthesize and high in yield, has wide adaptability to polymerization of large-steric-hindrance substituted olefin, and has high economic value.

4CzIPN-tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics

2,4,5,6-Tetrakis(3,6-di-tert-butyl-9H-carbazol-9-yl)isophthalonitrile (4CzIPN-tBu) was developed as a photocatalyst for the phosphorus-radical-initiated cascade cyclization reaction of isocyanides. By using 4CzIPN-tBu as catalyst, we developed a visible-light-induced proton-coupled electron transfer strategy for the generation of phosphorus-centered radicals, via which a wide range of phosphorylated phenanthridines, quinolines, and benzothiazoles were successfully constructed.

Scalable electrochemical synthesis of diaryliodonium salts

Cyclic and acyclic diaryliodonium are synthesised by anodic oxidation of iodobiaryls and iodoarene/arene mixtures, respectively, in a simple undivided electrolysis cell in MeCN-HFIP-TfOH without any added electrolyte salts. This atom efficient process does not require chemical oxidants and generates no chemical waste. More than 30 cyclic and acyclic diaryliodonium salts with different substitution patterns were prepared in very good to excellent yields. The reaction was scaled-up to 10 mmol scale giving more than four grams of dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate (>95%) in less than three hours. The solvent mixture of the large-scale experiment was recovered (>97%) and recycled several times without significant reduction in yield.

Direct photoexcitation of benzothiazolines: Acyl radical generation and application to access heterocycles

An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules.

Visible-Light-Induced Decarboxylative Cyclization/Hydrogenation Cascade Reaction to Access Phenanthridin-6-yl(aryl)methanol by an Electron Donor-Acceptor Complex

A novel and efficient visible-light-induced decarboxylative cyclization/hydrogenation cascade reaction of α-oxocarboxylic acids and 2-isocyanobiaryls has been developed. Without the need of any external photosensitizer, oxidant, and reductant, this method offers a mild and green approach for the synthesis of diverse alcohols in moderate to good yields. A mechanism indicated that an electron donor-acceptor complex-driven decarboxylation, radical addition/cyclization, and in situ photochemical reduction of ketones to alcohols could be involved in the reaction.

Regiospecific Introduction of Halogens on the 2-Aminobiphenyl Subunit Leading to Highly Potent and Selective M3 Muscarinic Acetylcholine Receptor Antagonists and Weak Inverse Agonists

Muscarinic M3 receptor antagonists and inverse agonists displaying high affinity and subtype selectivity over the antitarget M2 are valuable pharmacological tools and may enable improved treatment of chronic obstructive pulmonary disease (COPD), asthma, or urinary incontinence. On the basis of known M3 antagonists comprising a piperidine or quinuclidine unit attached to a biphenyl carbamate, 5-fluoro substitution was responsible for M3 subtype selectivity over M2, while 3′-chloro substitution substantially increased affinity through a σ-hole interaction. Resultantly, two piperidinyl-and two quinuclidinium-substituted biphenyl carbamates OFH243 (13n), OFH244 (13m), OFH3911 (14n), and OFH3912 (14m) were discovered, which display two-digit picomolar affinities with Ki values from 0.069 to 0.084 nM, as well as high selectivity over the M2 subtype (46-to 68-fold). While weak inverse agonistic properties were determined for the biphenyl carbamates 13m and 13n, neutral antagonism was observed for 14m and 14n and tiotropium under identical assay conditions.