Amination of Alkylboronic Esters

Abstract

Alkylboronic esters are high value chemical building blocks which can be used to make complex, C-sp³ rich molecules. The ability to convert the C−B bond in a range of C−C and C-heteroatom bond-forming reactions, in addition to their broad functional group compatibility, gives alkylboronic esters significant synthetic utility. Methods to convert boronic esters into amines have particular interest, due to the wide prevalence of nitrogen-based functional groups in biologically active compounds, functional materials, and catalysts. In this review, we explore different methods for the amination of alkylboronic esters. These can be split into three distinct classes based on the mechanism of reaction: amination through 1,2-metallate rearrangement, amination using nucleophilic ‘ate’ complexes, and oxidative amination reactions such as alkyl variants of the Chan-Lam reaction.