1355247-46-9

Usage

Physical state

Pale yellow solid

Molecular weight

211.27 g/mol

Common uses

Synthesis of pharmaceuticals and agrochemicals, intermediate in production of dyes and pigments

Stability

Stable under normal conditions

Solubility

Low solubility in water

Handling precautions

Harmful if swallowed or inhaled, can cause skin and eye irritation upon contact

Upstream product

• 138642-62-3 2-Cyanophenylboronic acid 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 172732-52-4 o-cyanophenylboronic acid-1,3-propylene glycol ester 
• 556-96-7 5-bromo-1,3-xylene 
• 100-47-0 benzonitrile 

Downstream Products

• 1448753-33-0 2-(3',5'-dimethylbiphenyl-2-yl)-1H-imidazole-4,5-dicarbonitrile 

Relevant academic research and scientific papers

The site-selectivity and mechanism of Pd-catalyzed C(sp2)-H arylation of simple arenes

Control over site-selectivity is a critical challenge for practical application of catalytic C-H functionalization reactions in organic synthesis. Despite the seminal breakthrough of the Pd-catalyzed C(sp2)-H arylation of simple arenes via a concerted metalation-deprotonation (CMD) pathway in 2006, understanding the site-selectivity of the reaction still remains elusive. Here, we have comprehensively investigated the scope, site-selectivity, and mechanism of the Pd-catalyzed direct C-H arylation reaction of simple arenes. Counterintuitively, electron-rich arenes preferably undergo meta-arylation without the need for a specifically designed directing group, whereas electron-deficient arenes bearing fluoro or cyano groups exhibit high ortho-selectivity and electron-deficient arenes bearing bulky electron-withdrawing groups favor the meta-product. Comprehensive mechanistic investigations through a combination of kinetic measurements and stoichiometric experiments using arylpalladium complexes have revealed that the Pd-based catalytic system works via a cooperative bimetallic mechanism, not the originally proposed monometallic CMD mechanism, regardless of the presence of a strongly coordinating L-type ligand. Notably, the transmetalation step, which is influenced by a potassium cation, is suggested as the selectivity-determining step.

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.