Pd(II)-catalyzed direct Csp3-H functionalization o.. (HINDAMINE)
Pd(II)-catalyzed direct Csp3-H functionalization of amines: a new platform for the synthesis of privileged molecules
Start date: Oct 1, 2014,
End date: Sep 30, 2016
Chemical synthesis, as central science, has a tremendous impact in Society by providing highly valuable compounds as new materials, drugs, sensors or sources of energy. Today, the way we get through those molecules is still a problem to solve. The development of novel methodologies for their efficient and straightforward construction is very relevant for Society, in the short, medium and long term. The last decade has seen the development of a new reactivity concept, taking advantage of the ubiquitous of C-H bond. The direct functionalization of this bond brings forth a more economical and faster way for the derivatization of organic compounds. Consequently, the design of metal catalyzed C-H bond functionalization has become a flourishing area in organic synthesis. This proposal details a design blueprint for palladium catalyzed direct Csp3-H bond functionalization of amines without the presence of any directing group. This will constitute a significant breakthrough in the field of metal catalyzed C-H bond functionalization allowing that “unfunctionalized” molecules become synthetic intermediates in synthesis. To achieve our goal we propose the use of easily accessible cyclic hindered amines as a new versatile platform for the functionalization of Csp3-H bonds. These cyclic cores are easily synthesized from the corresponding ketones and amino alcohols and therefore, after the corresponding functionalization step following by deprotection, we could access to γ-functionalized amino alcohols and β-functionalized ketones. Thus, the same chemical platform would allow us to functionalize two different families of important chemical compounds highlighting the impact that the technology presented in this proposal could have in the organic chemistry field. The work will therefore be multi-stranded, rich and broad and offer an excellent training to the Marie Curie Fellow.
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