Alkylboron Cross-Coupling Reactions

The ability to append alkyl moieties onto preexisting molecular scaffolds is of significant interest owing to the breadth of the diversified compounds that can be accessed in late stage synthesis. There are a number of procedures that are capable of incorporating alkyl subunits into organic molecules; however, many of these strategies are limited in scope. In particular, the highly reactive nature of organomagnesium compounds used in the Kumada–Corriu reaction limits their use to molecules that are virtually void of any reactive functional group. Less electropositive metals are also used in this context to overcome the limitations associated with highly reactive species; however, many of these organometallic reagents require careful in situ preparation and use, owing to their highly airand moisture-sensitive nature. In response to the growing need for a class of benchstable alkylmetal reagents, organotin and organoboron compounds have come to the fore. However, the perceived toxicity associated with organotin compounds has led to the B-alkyl Suzuki–Miyaura cross-coupling reaction becoming the platform of choice to accomplish this desired bond formation.