Perfluoroalkylphosphines and Arsines obtained by Pd-Catalyzed Cross-Coupling Reaction with Organoheteroatom Stannanes

MARIO N. LANTERI; ROBERTO A. ROSSI; SANDRA E. MARTÍN

JOURNAL OF ORGANOMETALLIC CHEMISTRY

Elsevier Science B.V.

Año: 2009 vol. 694 p. 3425 - 3430

0022-328X

<!-- /* Font Definitions */ @font-face {font-family:Batang; panose-1:2 3 6 0 0 1 1 1 1 1; mso-font-alt:바탕; mso-font-charset:129; mso-generic-font-family:auto; mso-font-format:other; mso-font-pitch:fixed; mso-font-signature:1 151388160 16 0 524288 0;} @font-face {font-family:"@Batang"; panose-1:0 0 0 0 0 0 0 0 0 0; mso-font-charset:129; mso-generic-font-family:auto; mso-font-format:other; mso-font-pitch:fixed; mso-font-signature:1 151388160 16 0 524288 0;} /* Style Definitions */ p.MsoNormal, li.MsoNormal, div.MsoNormal {mso-style-parent:""; margin:0cm; margin-bottom:.0001pt; mso-pagination:widow-orphan; font-size:10.0pt; font-family:Arial; mso-fareast-font-family:Batang; mso-bidi-font-family:"Times New Roman"; mso-fareast-language:KO;} @page Section1 {size:612.0pt 792.0pt; margin:70.85pt 3.0cm 70.85pt 3.0cm; mso-header-margin:36.0pt; mso-footer-margin:36.0pt; mso-paper-source:0;} div.Section1 {page:Section1;} --> Abstract. Pd-catalyzed cross-coupling reaction of organoheteroatom stannanes containing elements of the groups 15 (P, As) and 16 (Se) with perfluoroalkyl iodides (RfI) was studied. Herein, a one-pot two-step reaction to form P-Rf, As-Rf and Se-Rfbonds is reported. The stannanes n-Bu3SnZPhn (Z = P, As, Se; n = 1-2) were generated in situ by the reaction of the PhnZ- anion with n-Bu3SnCl. The cross-coupling reactions of these stannanes with RfI afforded C-heteroatom products, new perfluoroalkylarsines and perfluoroalkylselenides in good yields (47-90%) and perfluoroalkylphosphines in moderate yields (15-48%).