Tailoring Buchwald-type phosphines with pyrimidinium betaines as versatile aryl group surrogates

Ludovik Noël-Duchesneau (1, 2) , Noël Lugan (1) , Guy Lavigne (1) , A. Labande (1) , Vincent César (1)

1 LCC - Laboratoire de chimie de coordination
2 UT3 - Université Toulouse III - Paul Sabatier

A derivatization of dialkylbiarylphosphines consisting in the formal replacement of their distal aryl group by a pyrimidinium betaine is reported. Two achiral representatives of this new class of Buchwald-type phosphines have been successfully synthesized through two strategies. The first one is based on a last stage introduction of the phosphino moiety, and the second one consists in a modular, one-pot, three-step procedure starting from an o-bromoaryl phosphine. The resulting phosphines have been coordinated onto gold(I) and palladium(II) centers and have been employed as supporting ligands in Pd-catalyzed SuzukiMiyaura cross-coupling of aryl halide substrates.

Domaines: Chimie de coordination

Ludovik Noël-Duchesneau, Noël Lugan, Guy Lavigne, A. Labande, Vincent César. Tailoring Buchwald-type phosphines with pyrimidinium betaines as versatile aryl group surrogates. Organometallics, 2014, 33 (19), pp.5085-5088. ⟨10.1021/om5007819⟩. ⟨hal-02023150⟩