Synthesis and characterizations of <i>N</i>,<i>N</i>′‐bis(diphenylphosphino)‐2‐(aminomethyl)aniline derivatives: application of a palladium(II) complex as pre‐catalyst in Heck and Suzuki cross‐coupling reactions

Abstract

Abstract The reaction of 2‐(aminomethyl)aniline with 2 equivalents of PPh 2 Cl in the presence of Et 3 N, proceeds in CH 2 Cl 2 to give N , N ′‐bis(diphenylphosphino)‐2‐(aminomethyl)aniline 1 in good yield. Oxidation of 1 with aqueous H 2 O 2 , elemental sulfur or gray selenium gave the corresponding oxide, sulfide and selenide dichalcogenides [Ph 2 P(E)NHC 6 H 4 CH 2 NHP(E)Ph 2 ] (E: O, 2a; S, 2b; Se, 2c), respectively. The reaction of [Ph 2 PNHC 6 H 4 CH 2 NHPPh 2 ] with PdCl 2 (cod), PtCl 2 (cod) and [Cu(MeCN) 4 ]PF 6 gave the corresponding chelate complexes, PdCl 2 1, PtCl 2 1 and [Cu(1) 2 ]PF 6 . The new compounds were fully characterized by NMR, IR spectroscopy and elemental analysis. The catalytic activity of the Pd(II) complex was tested in the Suzuki coupling and Heck reactions. The Pd(II) complex catalyzes the Suzuki coupling and Heck reaction, affording biphenyls and stilbenes respectively, in good yields. Copyright © 2009 John Wiley &amp; Sons, Ltd.