915131-18-9

Upstream product

• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 1493-27-2 ortho-nitrofluorobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 143825-84-7 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane 
• 1311484-52-2 MIDA alkenyl-2-boronate 
• 98-81-7 1-bromovinylbenzene 
• 15163-59-4 potassium o-nitrobenzoate 
• 3058-46-6 1-ethylsulfanyl-2-nitrobenzene 
• 14900-39-1 phenylvinylboronic acid 

Downstream Products

• 1504-16-1 3-phenyl-1H-indole 

Relevant academic research and scientific papers

Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source

A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.

Reactivity of Carbenes in Aqueous Nanomicelles Containing Palladium Nanoparticles

Palladium nanoparticles ligated with inexpensive triphenylphosphine and amphiphile PS-750-M are suitable for exploring the reactivity of carbenes in aqueous nanomicelles. Nanocatalyst is highly selective for metal-carbene migratory insertion, and micelle

Palladium-catalyzed cross-coupling of aryl fluorides with N-tosylhydrazones via C-F bond activation

A palladium-catalyzed cross-coupling reaction of electron-deficient aryl fluorides with aryl N-tosylhydrazones has been reported. Mechanistically, this approach involves C-F bond activation and migratory insertion of palladium carbene as the two key steps

Vinylic MIDA boronates: New building blocks for the synthesis of aza-heterocycles

Abstract A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This novel synthetic approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif. Old dog, new tricks: A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif.

Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine

Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxy, and amino groups were tolerated. From β,β-disubstituted o-nitrostyrenes, 2,3-disubstituted indoles were formed by a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterize the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine. Mild and efficient treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-Hamination process. A concise synthesis of a marketed drug (rizatriptan) and a formal total synthesis of aspidospermidine featuring this novel N-heterocyclization process are reported.

Arylalkene synthesis via decarboxylative cross-coupling of alkenyl halides

A bimetallic catalyst system generated from readily available palladium(II) and copper(I) salts, 1,10-phenanthroline and tri-1-naphthylphosphine was found to efficiently mediate the decarboxylative cross-coupling of alkenyl bromides and chlorides with aromatic carboxylates. It allows the regiospecific synthesis of a broad range of aryl- and heteroarylalkenes in high yields.

Synthesis of nitrodienes, nitrostyrenes, and nitrobiaryls through palladium-catalyzed couplings of β-nitrovinyl and o-nitroaryl thioethers

A highly efficient, base-free, mild protocol for the palladium-catalyzed, copper-activated desulfitative couplings of vinyl and aryl β- nitrothioethers generates a wide variety of conjugated nitroorganics. Orthogonality to traditional Suzuki-Miyaura coupling is demonstrated, as well as synthetic utility, through reductive Cadogan cyclization, for the formation of indoles, carbazoles, and pyrroles.