Nickel-catalyzed regioselective hydroamination of unactivated alkenes

Abstract

Hydroamination, defined as an addition of a nitrogen atom and a hydrogen atom across a C−C multiple bond, represents a powerful synthetic tools with diverse advantages. In the case of unactivated alkenes substrate, however, it is hard to specify the reaction site by difficult discrimination of similar chemical environments. Thus, the development of a highly regioselective hydroamination reaction has consistently attracted significant attention for predicting the position of the C−N bond formed by hydroamination reaction. This thesis describes strategies capable of site-selective construction of C−N bond in unactivated alkenes using nickel catalysis. In chapter 1, nickel-catalyzed proximal-selective hydroamination of unbiased alkenes using a bidentate directing group is demonstrated. In chapter 2, nickel-catalyzed remote γ-C(sp$^3$)–H amination protocol of unactivated alkenes is discussed, highlighting the essential roles of chain walking and chelation-assisted strategies.