Novel Formaldimine Precursor for Use in a Hosomi-Sakurai Reaction for the Formation Of Phenyl-Substituted Homoallylamines And A New Modular Approach For The Synthesis Of Half-Sandwich Ruthenium Complexes
Mississippi State University
Date of Degree
Graduate Thesis - Open Access
Master of Science
College of Arts and Sciences
Department of Chemistry
Organometallic allylation for the formation of C-C bonds has been a widely developed area over the past several decades for the formation of homoallylic alcohols and amines. One such pathway, the eponymous Hosomi-Sakurai reaction involves the Lewis acid-catalyzed addition of an allylic silane to an acetal, carbonyl, or imine. This work demonstrates an example of a Hosomi-Sakurai reaction using 1,2-ditosyl diazetidine as a slow release formaldimine precursor with good yield and high selectivity. Another less classical field, C-H activation, has also been around for several decades, but has recently exploded in new innovations. Through C-H activation chemists are able to bypass the need for functional groups that are substituted out, but instead utilizes the C-H bond as a synthon for further functionalization. This work will also demonstrate a modular approach for the synthesis of several ruthenium complexes with the potential to catalyze C-H activation.
Baine, Jonathan, "Novel Formaldimine Precursor for Use in a Hosomi-Sakurai Reaction for the Formation Of Phenyl-Substituted Homoallylamines And A New Modular Approach For The Synthesis Of Half-Sandwich Ruthenium Complexes" (2018). Theses and Dissertations. 3314.