Site-selective catalytic functionalizations of unactivated alkenes using remote directing strategies

Abstract

The regioselective functionalization of alkenes, which are widely present in a variety of valuable compounds, is a powerful tool for effectively gaining molecular diversity in organic chemistry. However, the majority of the developed functionalization of unactivated alkenes still suffers from low reactivity and regioselectivity caused by the difficult discrimination of similar chemical environments. Therefore, this dissertation describes studies on the three catalytic reactions using remote directing strategies for site-selective functionalization of unactivated alkenes. In chapter 1, the site-selective 1,1-geminal difunctionalization of unactivated alkenes has been achieved through sequentially introducing two types of nucleophiles at the same position of an alkene using a remote directing group and cationic palladium catalysis. In chapter 2, the proximal-selective hydroamination of unactivated alkenes using a remote directing group and NiH catalytic system has been developed to synthesize unnatural amino acid derivatives. In chapter 3, photocatalytic site-selective 1,2-trifluoromethylative pyridylation of unactivated alkenes has been developed through inducing ortho-selective intramolecular migration on pyridyl ring.