Transition metal catalysed functionalisation of c=c through boron chemistry: a tandem approach

Identificador:  TDX:879

Handle: https://hdl.handle.net/20.500.11797/TDX879

Autors:  Lillo García, Vanesa

Resum:
Organoboron compounds are some of the most useful reagents in organic synthesis. The carbon-boron bond, once formed, can be cleaved in a variety of ways, with or without homologation, leading to a wide range of useful functional groups. The catalytic addition of H-B or B-B across to unsaturated C-C bond is one of the catalytic processes with higher selective control in the C-B bond formation. <br/>In the first Chapter of this thesis shows the evolution through the literature of the three main catalytic reactions of boron addition to alkenes, such as hydroboration, diboration and &#61538;-boration.<br/>Chapter 2 describes the first attempt at the catalytic asymmetric hydroboration in both homogeneous and heterogenised version of functionalised allylic system. In addition, the first example of the diboration reaction of these mentioned substrates with complexes based on Pt modified with NHC ligands is described.<br/>Chapter 3 discusses catalytic diboration of alkenes based on Cu, Pd and Ir- catalytic system modified with NHC ligands. The presence of a base and the use of an excess of diboron reagent are essential to obtain high degree of activity and selectivity.<br/>Chapter 4 shows the successful synthesis of chiral boron enolates by using inexpensive metals such as copper and nickel modified with chiral NHC ligands and modulated chiral commercially available diphosphines respectively. <br/> In Chapter 5 describes complexes containing transition metals such as platinum and palladium modified with NHC ligands and P,P respectively capable to perform the in situ tandem catalytic boron-addition-Suzuki-Miyaura cross-coupling.