Atom‐Efficient, Palladium‐Catalyzed Stille Coupling Reactions of Tetraphenylstannane with Aryl Iodides or Aryl Bromides in Polyethylene Glycol 400 (PEG‐400)

Abstract

Abstract:The Stille coupling of tetraphenylstannane with aryl iodides or aryl bromides using the bis(triphenylphosphine)palladium dichloride/sodium acetate/polyethylene glycol 400 [PdCl 2 A C H T U N G T R E N N U N G (PPh 3 ) 2 /NaOAc/ PEG-400] catalytic system at 100 8C has been developed. The reactions were carried out in an atom-efficient way, as 4 equivalents of aryl iodides or aryl bromides coupled effectively with 1 equivalent of tetraphenylstannane to furnish 4 equivalents of the corresponding functionalized biaryls in high yields.

Suzuki-Miyaura Reactions Catalyzed by C2-Symmetric Pd-Multi-Dentate N-Heterocyclic Carbene Complexes

“…13 C-NMR (101 MHz, CDCl 3 ) δ 166.96, 145.58, 139.94, 130.12, 128.94, 128.87, 128.16, 127.27, 127.03, 52.13 ppm. The NMR data are in agreement to those in literature [ 46 , 47 ].…”

“…13 C-NMR (101 MHz, CDCl 3 ) δ 141.37, 128.89, 127.38, 127.30 ppm. The NMR data were in agreement with those reported in literature [ 46 ].…”

A green and efficient method for synthesis of benzimidazoles using nano‐Fe3O4 in PEG‐400/H2O aqueous system under ambient conditions at room temperature

“…Polyethylene glycol (PEG), a commercially available, non‐toxic and recyclable polymer, has been widely used in organic transformation as an environmentally benign solvent, which is has potential as a substitute for volatile organic solvents, e.g. in N ‐arylation of amines, cross‐coupling reaction, asymmetric dihydroxylation, aldol reaction, Baylis–Hillman reaction and multi‐component condensation.…”

Boron Trifluoride Etherate Induced Stille Cross-Coupling Reaction of Aryltriazenes with Tributyl(phenyl)stannane Catalyzed by Recyclable Pd/C Catalyst

“…In the past several decades, the transitionmetal-catalyzed Stille cross-coupling reaction has evolved as a powerful synthetic tool for the synthesis of unsymmetrical biaryls 3 , which are widely present in numerous classes of organic compounds, such as natural products, polymers, advanced materials, liquid crystals, ligands and molecules of medicinal interest 4 . Most of the reported Stille reactions are based on the use of aryl halides [5][6][7] , triflates 8 , sulfonyl chlorides 9 , sulfonates 10 and carboxylates 11 as one of the reaction components. As an alternative candidate for the electrophilic coupling partner, arenediazonium salts have also been employed in place of aryl halides in the Stille cross-coupling reaction 12 , and show high activity.…”