35035-67-7

Upstream product

• 624-31-7 4-tolyl iodide 
• 1076-43-3 benzene-d6 
• 71-43-2 benzene 
• 106-38-7 para-bromotoluene 

Relevant academic research and scientific papers

C60-catalyzed direct C-H arylation of benzene with aryl iodides in air

C60 at 1 mol % loading catalyzed the direct C-H arylation of benzene with aryl iodides in air to yield biaryls. The in situ generation of electron-rich C60(OH)2-, from C60 and OH-, reduced the aryl iodides to aryl radicals for arylation of benzene. The large surface area and spherical shape of C60 facilitated this process.

Vasicine catalyzed direct C-H arylation of unactivated arenes: Organocatalytic application of an abundant alkaloid

Vasicine, a quinazoline alkaloid isolated from Adhatoda vasica, has been employed as an organocatalyst for direct C-H arylation of unactivated arenes with aryl iodides/bromides without the assistance of any transition metal catalyst. A number of sensitive functional groups such as methyl, methoxy, O-benzyl, acetyl, and amino were well tolerated under present reaction conditions. Mechanistic investigation supported the involvement of radical intermediates.

Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes

An amino-linked nitrogen heterocyclic carbene (amino-NHC), 1-tBu, has been shown to mediate carbon-carbon coupling through the direct C-H functionalization of benzene and pyridine in the absence of a metal catalyst. Using EPR, the first spectroscopic evidence corroborating the single electron transfer mechanism for the metal-free carbon-carbon coupling manifold, as reported by others, is introduced.

Assessment of the intermediacy of arylpalladium carboxylate complexes in the direct arylation of benzene: Evidence for C-H bond cleavage by "ligandless" species

Palladium-catalyzed direct arylations of benzene have been proposed to occur by the generation of a phosphine-ligated arylpalladium pivalate complex LPd(Ar)(OPiv) and reaction of this complex with benzene. We have isolated an example of the proposed intermediate and evaluated whether this complex does react with benzene to form the biaryl products of direct arylation. In contrast to the proposed mechanism, no biaryl product was formed from cleavage of the benzene C-H bond by LPd(Ar)(OPiv). However, reactions of LPd(Ar)(OPiv) with benzene and additives that displace or consume the phosphine ligand formed the arylated products in good yield, suggesting that a "ligandless" arylpalladium(II) carboxylate complex undergoes the C-H cleavage step. Consistent with this conclusion, we found that reactions catalyzed by Pd(OAc)2 without a ligand occur faster than, and with comparable selectivities to, reactions catalyzed by Pd(OAc)2 and a phosphine ligand.

New ligands that promote cross-coupling reactions between aryl halides and unactivated arenes

Several ligands were designed to promote transition-metal-free cross-coupling reactions of aryl halides with benzene derivatives. Among the systems probed, quinoline-1-amino-2-carboxylic acid was found to serve as an excellent catalyst for cross-coupling between aryl halides and unactivated benzene. Reactions using this inexpensive catalytic system displayed a high functional group tolerance as well as excellent chemoselectivities.

Iron-catalyzed direct arylation through an aryl radical transfer pathway

(Figure Presented) A general and efficient iron-catalyzed direct arylation of benzene and hetereoaryl derivatives using a cost-effective and environmentally benign catalyst is described. The reaction is performed under neat conditions and can proceed at room temperature.

Tert-butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1,10-phenanthroline derivative

Sodium tert-butoxide mediates the coupling of aryl halides with benzene derivatives without the aid of transition metal catalysts but with a catalytic 1,10-phenanthroline derivative.