Organoheteroatom Stannanes in Palladium-Catalyzed Cross-Coupling Reactions with 1-Naphthyl Triflate
作者:Mariana Bonaterra、Roberto A. Rossi、Sandra E. Martín
DOI:10.1021/om8009816
日期:2009.2.9
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)Z(-) anion with n-Bu3SnCl. 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 PPh3 ligand proved to be particularly effective in enhancing the coupling reaction.