New study of the reactivity and selectivity of boron reagent's in the rhodium catalyzed 1,4-addition

Identifier:  TFG:295

Handle: https://hdl.handle.net/20.500.11797/TFG295

Authors:  Cervellera Dominguez, Ander

Abstract:
Abstract The Hayshi-Miyaura reaction was discovered in 1997 by Miyaura and co-workers, offered a highly attractive alternative to the traditional coper catalysed conjugated addition to enones. This rhodium catalysed reaction, showed to be tolerant to different variety of functional groups, took place under mild conditions, was insensitive to water and employed mild organoboranes which do not undergo 1,2-addition as a side reaction. Building on the previous work of our group about the relative reactivity of the borane based reagents with vinyl pyrazines as a highly reactive substrate, different studies have been carried out with same or lower reactivity substrates. Showing a generality in the selectivity of different boron based reagents for high and low reactivity substrates. Becoming really interesting for further synthetic application for One-Pot reaction. On the other hand, the idea of a new tranmetalation mechanism for the trifluoro boron reagent when the reaction media is base-free has been outlined.