Tim Scarella ‘08
Advisor: Dr. Thomas Mitzel

INVESTIGATIONS IN INDIUM METAL-PROMOTED COUPLING REACTIONS: ATTEMPTED CONTROL OF PRODUCT FORMATION IN COUPLING REACTIONS WITH 1,3-DIBROMOPROPENE AND COUPLING OF ALLYLINDIUM REAGENTS TO IMINES

Abstract:

Indium-promoted coupling reactions are among a class of metal-promoted coupling reactions that have proved to be versatile and convenient for use in organic synthesis. Previous work in the Mitzel laboratory has shown that indium promoted coupling reactions with aldehydes proceed with high stereo- and regio-selectivity. Additionally, achieving control of product formation in a system where it is reasonable to predict the formation of more than one product is of paramount importance in organic chemistry. To this end, the first part of this thesis will discuss attempts to control product formation in indium promoted couplings using changes in solvent, according to the scheme below.

Since reactions with indium have been shown to work well with aldehydes, another area of interest is reaction with imines. The second part of this thesis will describe investigations of indium promoted coupling reactions with imines.