A general diastereoselective synthesis of highly functionalized ferrocenyl ambiphiles enabled on a large scale by electrochemical purification

Emmanuel Lerayer (1) , Patrice Renaut (1) , Julien Roger (1) , Nadine Pirio (1) , Hélène Cattey (1) , Charles H. Devillers (1) , Dominique Lucas (1) , Jean-Cyrille Hierso (1, 2)

1 ICMUB - Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon]
2 IUF - Institut universitaire de France

A general synthesis of highly functionalized ferrocenes, which include (P,B)- and (N,B)-ambiphiles, has been developed at a multigram scale. Diastereoselective stepwise modification of di-tert-butylated ferrocenes included the unprecedented separation of electroactive species. Bulky alkyl groups on ferrocenes ensure planar chirality of ambiphiles and enforce closer proximity of antagonist Lewis functions.

Mots clés: complexes, palladium, ligands, carbon-dioxide, aryl bromides, free hydrogen activation, frustrated lewis pairs, coordination chemistry, catalytic applications, direct arylation

Domaines: Chimie de coordination

Emmanuel Lerayer, Patrice Renaut, Julien Roger, Nadine Pirio, Hélène Cattey, et al.. A general diastereoselective synthesis of highly functionalized ferrocenyl ambiphiles enabled on a large scale by electrochemical purification. Chemical Communications, 2017, 53 (44), pp.6017-6020. ⟨10.1039/c7cc02469j⟩. ⟨hal-03473696⟩