1127212-97-8

Upstream product

• 230-27-3 7,8-benzoquinoline 
• 21436-44-2 3-methylbenzoic acid anhydride 
• 108-41-8 1-chloro-3-methylbenzene 
• 1015758-32-3 ethyl benzo[h]quinoline-10-carboxylate 
• 17933-03-8 m-tolylboronic acid 
• 625-95-6 3-Iodotoluene 
• 591-17-3 meta-bromotoluene 
• 28987-79-3 m-tolylmagnesium bromide 

Relevant academic research and scientific papers

Rhodium-catalyzed decarbonylation cross-coupling reactions of aromatic aldehydes and arylboronic acids via C–C bond activation directed by a guide group chelation

A rhodium-catalyzed decarbonylative cross-coupling reaction of benzoquinoline-10-carbaldehydes with arylboronic acids through chelation-assisted sp2 C–CHO bond activation has been developed. A variety of functional groups substituted phenylboronic acids or benzoquinoline-10-carbaldehydes are compatible with the reaction under the optimized reaction conditions, the corresponding 10-phenylbenzo[h]quinoline derivatives were obtained in moderate to good yields. The method affords a useful strategy for the synthesis of N-heterocyclic biaryl compounds via rhodium-catalyzed sp2 C–CHO bond activation.

Expeditious and Solvent-Free Nickel-Catalyzed C?H Arylation of Arenes and Indoles

An efficient solvent-free nickel-catalyzed method for C?H bond arylation of arenes and indoles has been developed, which proceeds expeditiously through chelation assistance. The reaction is highly selective for mono-arylation and tolerates sensitive and structurally diverse functionalities, such as halides, ethers, amines, indole, pyrrole and carbazole. This reaction represents the first example of a nickel-catalyzed C?H arylation by monochelate assistance and symbolizes a rare precedent in solvent-free C?H arylation. Mechanistic investigations by various controlled reactions, kinetic studies, and deuterium labeling experiments suggest that the arylation follows a single electron transfer (SET) pathway involving the turnover-limiting C?H nickelation process.

Site-selective C-H/C-N activation by cooperative catalysis: Primary amides as arylating reagents in directed C-H arylation

Direct C-H arylation of nonacidic C(sp)-H bonds with primary amides as arylating reagents via highly chemoselective C-H/C-N/C-C cleavages has been accomplished for the first time. The key to the success is the cooperative combination of rhodium(I) catalys

Efficient Approach to Construct Unsymmetrical Biaryls through Oxidative Coupling Reactions of Aromatic Primary Alcohols and Arylboronic Acids with a Rhodium Catalyst

Unsymmetrical biaryls were synthesized by oxidative coupling reactions between aromatic primary alcohols and arylboronic acids through the C-C bond cleavage of the primary alcohols chelated with a rhodium catalyst. The desired unsymmetrical biaryl products were obtained in good to excellent yields under the optimized reaction conditions. A wide variety of functionalities are compatible with the reaction under the optimized conditions. This new coupling strategy provides a favorable method to construct valuable biaryl compounds from aromatic primary alcohols which are cheap, environmentally friendly, and easily accessible substrates.

Cobalt-catalyzed C-H bond functionalizations with aryl and alkyl chlorides

Inexpensive cobalt catalysts derived from N-heterocylic carbenes (NHC) allowed efficient catalytic C-H bond arylations on heteroaryl-substituted arenes with widely available aryl chlorides, which set the stage for the preparation of sterically hindered tr

Rhodium-catalyzed cross-coupling reactions of carboxylate and organoboron compounds via chelation-assisted C-C bond activation

A new rhodium-catalyzed decarbonylated coupling reaction of ethyl benzo[h]quinoline-10-carboxylate and organoboron compounds that occurs through chelation-assisted sp2 C-COOEt bond activation was described. In this system CuCl played a very important role, and a five-membered rhodacycle was also involved as a key intermediate. Various functionalities were compatible in the reaction, and the desired products were obtained in good to excellent yields. DFT calculations on the mechanisms of this reaction using a Rh(I) model catalyst have also been carried out.

Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium

2-Arylpyridines, 2-alkenylpyridine, and aromatic imines can be coupled with aryl bromides in the presence of an iron catalyst, metallic magnesium, a diamine ligand and an organic dihalide oxidant at 0 °C. The use of a 1:1 mixture of tetrahydrofuran and 1,

Direct cross-coupling of C-H bonds with grignard reagents through cobalt catalysis

Go go Grignard! The first highly regioselective, cobalt-catalyzed C-H transformation of benzo[h]quinoline and phenylpyridine derivatives with Grignard reagents at room temperature has been achieved (see scheme). Both aryl and alkyl Grignard reagents showed significant reactivity.

RuCi3 xH2O-catalyzed direct arylation of arenes with aryl chlorides in the presence of triphenylphosphine

A study was conducted to demonstrate the RuCl3·xH 2O catalytic system for direct arylation of arenes with aryl chlorides. The phenylation of benzo[h]quinoline with chlorobenzene was investigated under preliminary studies. The reaction of benzo[h]quinoline and chlorobenzene N-methyl-2-pyrrolidone (NMP) formed Ph as the only product in 86-93% yields at 120-130 8C in the presence of K2CO3 using 5 mol% RuCl3·xH2O and 10 mol% PPh3. It was observed that the presence of an excess of ligand did not affect formation of Ph, while sub-stoichiometric ligand amounts led to a reduced conversion for benzo[h]quinoline. The arylation and benzylation of benzo[h]quinoline with various aryl chlorides was also investigated under the study.

Efficient Rh(I)-Catalyzed direct arylation and alkenylation of arene C-H bonds via decarbonylation of benzoic and cinnamic anhydrides

Efficient rhodium(I)-catalyzed regioselective direct arylation and alkenylation of aromatic C-H bonds has been realized with aromatic carboxylic and cinnamic anhydrides as the coupling partners via decarbonylation and C-H activation under phosphine-free c