88659-28-3Relevant articles and documents
Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
Quinteros, Gisela J.,Uberman, Paula M.,Martín, Sandra E.
, p. 2698 - 2705 (2015/04/27)
Biphenyl-based arsine ligands were prepared in two-step fashion by Pd-catalyzed arsination and microwave-assisted Suzuki-Miyaura coupling, providing sterically demanding arsine ligands in overall isolated yields up to 82 % as air-stable solids. Short reaction times were achieved with the assistance of microwave irradiation in the direct and simple described protocol for the synthesis of biarylarsine ligands. The activities of the biphenyl arsine ligands were explored in Pd-catalyzed Heck coupling. As a general trend, the ligands with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone performed more efficiently in the coupling reaction. This catalytic system allowed several interesting stilbenes to be obtained in very good yields. Sterically demanding biphenyl-based arsine ligands were prepared in high overall yields by microwave-assisted Suzuki-Miyaura coupling. The ligands were evaluated in the Pd-catalyzed Heck coupling reaction; the most active were those with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone.
Phosphides and Arsenides as Metal-Halogen Exchange Reagents. Part 2. Reactions with Aromatic Dihalides
Gillespie, Donal G.,Walker, Brian J.,Stevens, David,McAuliffe, Charles A.
, p. 1697 - 1703 (2007/10/02)
1,2-Dihalogenobenzenes react with two molar equivalents of lithium diphenylphosphide in the presence of furan to give, after oxidation, triphenylphosphine oxide (major) and the corresponding 2-halogenophenyldiphenylphosphine oxide.No trace of furan-dehydrobenzene adduct was observed in these reactions; however, 1- and 2-naphthyldiphenylphosphine oxides (9:4) were detected.These compounds were the major products from the reaction of the furan-dehydrobenzene adduct with diphenylphosphide, although the ratio of 1- to 2-isomers was quite different (1:9) in this case.Reaction of lithium diphenylphosphide with 3,4-dichloronitrobenzene gave tetrachloroazobenzene (40percent) as the only isolated product and attempts to replace 1,2-dihalogenobenzenes with 2-halogenobenzenediazonium salts gave much lower yields of products.Although dehydrobenzene is thought to be involved in many of these reactions, alternative mechanisms also operate, depending on the halides used.The reaction of lithium diphenylarsenide with 1,2-dihalogenobenzenes gave triphenylarsine as the major product and it seems likely that similar mechanisms to those involved in reactions of diphenylphosphide are operating.Surprisingly, dehydrobenzene-furan adduct reacted with diphenylarsenide to give naphthalene in high yield.
