21498-52-2

Upstream product

• 3095-87-2 bromodiphenylarsine 
• 703-55-9 1-naphthylmagnesiumbromide 
• 829-83-4 diphenylarsane 
• 130-14-3 sodium 1-naphthalenesulfonate 
• 90-11-9 1-Bromonaphthalene 
• 21498-51-1 Potassium Diphenylarsenide 
• 603-32-7 triphenyl-arsane 
• 90-14-2 1-Iodonaphthalene 
• 99747-74-7 1-naphthyl triflate 
• 101319-72-6 n-Bu₃SnAsPh₂ 

Downstream Products

• 17316-47-1 Diphenyl-naphthyl-⁽¹⁾-arsin-sulfid 
• 21498-58-8 [1]naphthyl-diphenyl-arsine oxide 

Relevant academic research and scientific papers

One-pot palladium-catalyzed cross-coupling reaction of aryl iodides with stannylarsanes and stannylstibanes

(Formula presented) The reaction of Ph3As and Ph3Sb with Na metal in liquid ammonia gives Ph2M- ions (M = As, Sb) that react with n-Bu3SnCl to afford n-Bu3Sn-MPh 2 (1). The ammonia was allowed to evaporate, and toluene was added. The Pd-catalyzed cross-coupling reactions of these stannanes with aryl iodides afford functionalized triaryl-arsanes and triaryl-stibanes in high yields in a one-pot procedure (80-99%). The use of the commercially available, air-stable, and inexpensive Ph3M as the initial reagent and the one-pot process make this method a useful approach. This is the first report on the synthesis of 1 and the exploration of its chemistry.

Photostimulated Reaction of Diphenylarsenide and Diphenylstibide Ions with Haloaromatic Compounds by the SRN1 Mechanism. Electron Transfer vs. Bond Breaking of the Radical Anion Intermediate

Photostimulated reactions of haloaromatic compounds with potassium diphenylarsenide and potassium diphenylstibide were studied in liquid ammonia. 1-Bromonaphthalene and 9-bromophenanthrene reacted with diphenylarsenide ion to give four products: triphenylarsine, diphenylarylarsine, phenyldiarylarsine, and triarylarsine (aryl = 1-naphthyl and 9-phenanthryl); with 2-chloroquinoline as substrate only the straightforward substitution product 2-qiunolyldiphenylarsine was formed. p-Bromoanisole and 4-chlorobenzophenone reacted with potassium diphenylstibide to give four stibines: triphenylstibine, diphenylarylstibine, phenyldiarylstibine, and triarylstibine (aryl = p-anisyl and 4-benzoylphenyl).These reactions are believed to occur by the SRN1 mechanism with an extra feature of reversible coupling of aryl radicals with arsenide and stibide ions, which causes the scrambling of aryl rings.It is suggested that the low-lying ?* MO of the quinolyl moiety prevents C-As bond breaking of the radical anion intermediate.