Final Report for: "Bis-pi-allylpalladium Complexes in Catalysis of Multicomponent Reactions"

Malinakova, H. C. ; Shiota, Atsushi

关键词: AMINES;    BORONIC ACIDS;    CATALYSIS;    CATALYSTS;    IMINES;    PALLADIUM;    REACTION KINETICS;    SYNTHESIS cyclopalladated complexes;    allylpalladium complexes;    nucleophilic allylation;    homoallylic amines;    three-component coupling;   

DOI  :  10.2172/1044605
RP-ID  :  DOE/ER/15792-3
PID  :  OSTI ID: 1044605
Others  :  TRN: US201215%%171

学科分类：化学（综合）

美国|英语

来源: SciTech Connect

【 摘 要 】

The research project involved the development of new and functionally improved Pd(II) catalyst for a three-component reaction of boronic acids, allenes and imines to afford homoallylic amines that are useful in synthesis of biologically active heterocycles. Furthermore, insights into the reaction mechanism and the structure and reactivity of the catalytically active intermediates involved in this process were sought. As a result of this work, a new type of Pd-catalysts possessing an auxiliary ligand attached to the Pd center via a C-Pd and N-Pd bonds were identified, and found to be more active than the traditional catalysts derived from Pd(OAc)2. The new catalysts provided an access to a broader range of homoallylic amine products. Although the final unequivocal evidence regarding the structure of the Pd(II) complex involved in the nucleophilic transfer of the allyl fragment from the palladium center to the imine could not be obtained, mechanistic insights into the events that are detrimental to the activity of the originally reported Pd(OAc)2-based catalytic systems were uncovered.