Pd(PPh₃)₄-PEG 400 Catalyzed Protocol for the Atom-Efficient Stille Cross-Coupling Reaction of Organotin with Aryl Bromides

Abstract

Aryl bromides (4 equiv) were coupled efficiently with organotin (1 equiv) in an atom-efficient way using the tetra(triphenylphosphine)palladium/polyethylene glycol 400 (Pd(PPh3)4/PEG 400) catalytic system in the presence of sodium acetate (NaOAc) as base at 100 degrees C, providing excellent yields of the corresponding functionalized biaryls in short reaction times.

Ionic Liquid Supported Organotin Reagents: Green Tools for Stille Cross‐Coupling Reactions with Brominated Substrates

“…Reactions involving naphthyl as well as styrenyl and benzothiophene derivatives afforded good results in spite of difficulties concerning their isolation (Table 4, Entries 7-11). Indeed, contrary to Wang's report, [14] isolation of 2-phenylnaphthalene (23; Table 4, Entry 8) by flash chromatography failed because of its similar polarity with biphenyl byproduct 6.…”

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 ].…”

An Efficient Microwave-Assisted Suzuki Reaction using a New Pyridine-Pyrazole/Pd(II) Species as Catalyst in Aqueous Media

“…The crude material was flash chromatographed on a silica gel column. All of the compounds have been characterized by comparing 1 H-NMR with the values found in the literature [ 35 , 36 , 37 , 38 , 39 , 40 , 41 ].…”