Synthesis, Characterization, and Transformations of α-Borylcarbonyl Compounds Containing 1,2-Azaborine

Abstract

Organoboron compounds are widely used in organic synthesis and medicinal chemistry. It has been shown that organoboron compounds can undergo a vast quantity of transformations, especially stereospecific reactions. Boron enolates and their reactivity are less explored in the field of organic chemistry. In enolates, boron can be bound to oxygen or carbon. The boron-carbon enolates are of interest for having the potential to engage in stereospecific organoboron chemistry via the stereospecific carbon connected to the boron atom. Two methods of synthesizing boron-carbon enolates are through quaternized and unquaternized boron centers. While quaternized boron-carbon enolates are more studied, unquaternized boron-enolates represent a gap in the field. To date only four unquaternized boron-carbon enolates have been isolated and characterized with only one of the compounds engaging in organoboron chemistry. Herein I report the synthesis, isolation, and characterization of a boron-carbon enolate containing 1,2-azaborine as the organoboron analog.