[reaction: see text] The reaction of Ph(3)As and Ph(3)Sb with Na metal in liquid ammonia gives Ph(2)M(-) ions (M = As, Sb) that react with n-Bu(3)SnCl to afford n-Bu(3)Sn-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 Ph(3)M 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.
We haVe studied the Pd-catalyzed cross-coupling reaction of organoheteroatom stannanes containing elements of groups 15 (P, As, Sb) and 16 (Se) with 1-naphthyl triflate (3). The stannanes n-Bu 3 SnZPh n (Z ) P, As, Sb, Se; n ) 1, 2) were synthesized by the reaction of the Ph n Zanion with n-Bu 3 SnCl. The cross-coupling reactions of these stannanes with 3 in a one-pot procedure afforded the C-heteroatom products Ph n Z-1-Naph in good yields for Z ) As, Se (90 and 70% yields, respectiVely) and moderate yields for Z ) P (51% yield). Only 18% of 1-naphthyldiphenylstibine was obtained. Optimization studies reVealed that the combination of LiCl and free PPh 3 ligand proVed to be particularly effectiVe in enhancing the coupling reaction.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.