66252-14-0

Upstream product

• 90-14-2 1-Iodonaphthalene 
• 2042-37-7 o-cyanobromobenzene 
• 873-32-5 2-Chlorobenzonitrile 
• 13922-41-3 1-Naphthylboronic acid 
• 31892-41-8 N-cyano-benzimidazole 
• 138642-62-3 2-Cyanophenylboronic acid 
• 172732-52-4 o-cyanophenylboronic acid-1,3-propylene glycol ester 

Downstream Products

• 1383378-71-9 3-(p-tolyl)-4'H-spiro[isoindole-1,1'-naphthalen]-4'-one 
• 82-05-3 7H-benz[d,e]anthracene-7-one 
• 6051-98-5 7H-benzo[c]fluoren-7-one 

Relevant academic research and scientific papers

Novel syntheses of fluorenones via nitrile-directed palladium-catalyzed C-H and dual C-H bond activation

Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.

Metal-free directed ortho C-H iodination: Synthesis of 2'-iodobiaryl-2- carbonitriles

Metal-free directed ortho C-H iodination of biaryl-2-carbonitriles was developed. A series of 2'-iodobiaryl-2-carbonitriles were synthesized from substituted biphenylcarbonitriles and naphthylbenzonitriles in reasonably good yields by using bis(pyridine)iodonium(I) tetrafluoroborate (IPy 2BF4, Barluenga's reagent) and HBF4· OEt2. The biaryl-2-carbonitriles are useful precursors for the synthesis of benzocyclic ketones. Metal-free directed ortho C-H iodination of biaryl-2-carbonitriles is efficiently performed in good yields by using bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4, Barluenga's reagent) and HBF4·OEt2. Copyright

Copper-catalyzed aerobic spirocyclization of biaryl-N-H-imines via 1,4-aminooxygenation of benzene rings

A synthetic method of azaspirocyclohexadienones has been developed through copper-catalyzed aerobic spirocyclization of biaryl-N-H-imines prepared by the reaction of biarylcarbonitriles and Grignard reagents.

A convenient synthesis of benzonitriles via electrophilic cyanation with N-cyanobenzimidazole

(Chemical Equation Presented) Couplings: N-Cyanobenzimidazole has been used in the synthesis of aryl- and heteroarylnitriles from the corresponding Grignard reagents (see scheme). This electrophilic cyanation is further extended to the synthesis of 2-cyano1,1'-biaryls through a domino Grignard-coupling/ cyanation strategy.

Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand

A novel bis-phenanthryl N-heterocyclic carbene (NHC) based palladium acetate catalyst was effective for the coupling of various aryl and vinyl chlorides with organoboron compounds. N,N-Bis-(2,9-dicyclohexyl-10-phenanthryl)- 4,5-dihydroimidazolium chloride 8 (H2ICP·HCl) with Pd(OAc)2 and KF·18-c-6 in THF at room temperature gave Suzuki-Miyaura coupling of aryl and vinyl chorides, including unactivated and di-ortho substituted substrates in high yields. Hindered tri- and tetra-ortho substituted products were also efficiently produced. Benzyl chloride was also found to be a useful coupling partner and trimethylboroxine was used to give methylated products. The effect of ligand, base, temperature, solvent, and reaction time are reported along with various substrates including halides and triflates.

Preparation of unsymmetrical biaryls via palladium-catalyzed coupling reaction of aryl halides

The synthesis of unsymmetrical biaryls is achieved using Pd(OAc)2 as the catalyst. A great variety of aryl halides having electron withdrawing and electron donating functional groups in para, meta and ortho positions have been successfully coupled.