1051472-55-9

Upstream product

• 100-42-5 styrene 
• 123248-22-6 butyl p-chlorocinnamate 
• 141-32-2 acrylic acid n-butyl ester 
• 586-75-4 4-chlorobenzoyl chloride 
• 591-50-4 iodobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 91911-22-7 butyl (E)-4-bromocinnamate 
• 106-39-8 bromochlorobenzene 
• 42175-12-2 butyl (E)-4-chlorocinnamate 

Relevant academic research and scientific papers

N-Acylsaccharins as Amide-Based Arylating Reagents via Chemoselective N-C Cleavage: Pd-Catalyzed Decarbonylative Heck Reaction

Palladium-catalyzed decarbonylative Heck reaction of amides by chemoselective N-C activation using N-acylsaccharins as coupling partners has been accomplished. These studies represent only the second example of amide-Heck reactions reported to date. A broad range of electronically diverse amide and olefin coupling partners is amenable to this transformation. Orthogonal site-selective Heck cross-couplings by C-Br/N-C cleavage and mechanistic studies are reported. This report introduces readily available, bench-stable, cheap, and benign N-acylsaccharins as aryl transfer reagents to access versatile aryl-metal intermediates.

Heck, Sonogashira, and Hiyama reactions catalyzed by palladium nanoparticles stabilized by tris-imidazolium salt

Palladium nanoparticles, prepared by the hydrogenation of Pd(dba) 2 in the presence of a tris-imidazolium iodide as stabilizer, act as an efficient catalyst for Heck and copper-free Sonogashira reactions with a range of aryl iodides and bromides at 0.2 mol-% Pd loading. Moreover, we describe a convenient protocol for the fluoride-free Hiyama coupling of vinylsilanes with aryl iodides that involves the use of sodium hydroxide as promoter in a methanol/water mixture. Under the developed conditions, one-pot, double Heck and Hiyama-Heck reactions are successfully achieved.

Pd nanoparticle catalysed one-pot sequential Heck and Suzuki couplings of bromo-chloroarenes in ionic liquids and water

Pd nanoparticles generated in green reaction media (viz. ionic liquids and water) catalyze the one-pot sequential Heck and Suzuki coupling reactions of bromo-chloroarenes to afford unsymmetrically substituted arenes in good yields.

Efficient heck reactions catalyzed by palladium(0) and -(II) complexes bearing n-heterocyclic carbene and amide functionalities

A palladium(0) NHC complex Pd0(LH1)2(MA) (MA = maleic anhydride) was prepared from the amide-imidazolium salt [LH 1H2]Cl (H1 = NH proton; H2 NCHN proton). The X-ray diffraction studies confirmed that a η2-MA ligand and two monodentate NHC ligands with the H1 protons remaining intact are coordinated. These NH protons are involved in intra- or intermolecular hydrogen bonds stabilizing the solid-state structure. Degradation of Pd(LH1)2(MA) in air leads to the formation of the chelate complex trans-PdIIL2 and other unidentified products. Negative-ion electrospray mass spectrometry revealed some intriguing Pd(0) species, including a 14-electron [Pd0L]- species that bears only a bidentate NHC/amido ligand. The anionic amido group imparts a high electron density on a palladium center, as shown by X-ray photoelectron study. The palladium(0) precatalyst is highly efficient in catalyzing Heck reactions with activated aryl chlorides in ionic liquid. For deactivating aryl chlorides and bulky aryl bromides, cis-PdIIL2 is more effective. A range of Heck-coupled products can be prepared by Pd 0(LH1)2(MA) and cis-PdIIL 2. The latter complex also successfully mediates one-pot sequential Heck/Heck and Suzuki/Heck coupling reactions with 4-bromochlorobenzene as substrate.

Pd-catalyzed efficient one-pot sequential cross-coupling reactions of aryl dihalides

(Chemical Equation Presented) The palladium complex containing N-heterocyclic carbene ligands catalyzes one-pot sequential Heck/Suzuki, Heck/Heck, and Heck/Sonogashira coupling reactions of aryl dihalides to afford unsymmetrically substituted arenes in ex