Straightforward and Recyclable System for Synthesis of Biaryl Ketones via Carbonylative Coupling Reactions of Aryl Halides with PhB(OH)₂ and (EtO)₃ PhSi

Abstract

Solvent‐dispersible magnetite (Fe3O4) chitosan‐functionalized with methionine was effectively prepared to immobilize Pd(0) with a metal adsorption method. The catalyst was characterized by Transmission Electron Microscopy (TEM), Field emission scanning electron microscopy (FE‐SEM), Powder X‐ray Diffraction (XRD), Energy Dispersive X‐ray spectroscopy (EDX), FT‐IR spectra, thermogravimetric analyzer (TGA) and vibrating sample magnetometer (VSM). A variety of biaryl ketones were conveniently synthesized in good to high yields via carbonylative coupling of aryliodides with phenylboronic acid and PhSi(OEt)3 as phenylating reagents in the presence of Mo(CO)6 as a carbon monoxide reagent. Both electron‐rich and electron‐poor aryl iodides gave diaryl ketones in excellent yields and the catalytic system can be reused up to eight times.

Advances in Transition‐Metal Catalyzed Carbonylative Suzuki‐Miyaura Coupling Reaction: An Update

“…Hajipour and co‐workers [61] developed the solvent‐dispersible magnetite (Fe 3 O 4 )‐Pd(0)nanoparticles complex functionalized with methionine and chitosan. The characterization of the catalyst was performed by TEM, FE‐SEM, Powder XRD, EDX, FT‐IR spectra, TGA and VSM in order to prove the deposition of palladium(0) nanoparticles over the magnetic support.…”

NCN–Pincer–Pd Complex as Catalyst for the Hiyama Reaction in Biomass-Derived Solvents

“…Some approaches to the Hiyama coupling in neoteric solvents include the use of water as the reaction medium, usually under reflux conditions, using a phase transfer catalyst or with highly activated starting materials, such as diazonium salts. − Ionic liquids, which share some of the advantages of DESs, but with the drawbacks of being highly toxic and economically expensive, have also been recently investigated as reaction media. A Hiyama-type reaction in ionic liquids was described by Bäuerlein et al, using 10 mol % of a Pd precursor, 20 mol % of a complex ligand, and 4 equiv of a fluoride salt .…”

A Facile synthesis of Biaryl ketones in recyclable system: Triazenes as new coupling partners in the carbonylative Suzuki and Hiyama cross‐coupling reactions using NFSac as CO source

“…al . reported a mild and operationally simple heterogeneous carbonylative Suzuki and Hiyama coupling reactions of aryl halide using ImmPd(0)‐MNPs used as catalytic system which can be removed easily by an external magnet and reusable for several cycles under fluoride‐free conditions [9b] . In all the previous strategies aryl halides were used as arene sources, while in the present work, various triazenes have been utilised as new arene sources in carbonylative Suzuki and hiyama cross coupling reactions.…”

“…Among various widely known carbonylative reactions, [3g,7a–d] particularly carbonylative Suzuki [8a–g] and carbonylative Hiyama couplings [9a–b] are of our interest. “Carbonylative coupling reactions” are the cross‐coupling reactions between two coupling partners that result in the formation of two new carbon‐carbon bonds in the presence of carbon monoxide (CO).…”