Beginning with the advent of the hydroboration reaction nearly 70 years ago, a variety of transformations have been developed to add B�X s bonds to C�C multiple bonds. The boronic acid derivatives produced through these methods are versatile intermediates in organic synthesis. Notably, a related process for B�O s bond addition has yet to be reported, although such a reaction could be useful in generating ether-containing organoboron products. Herein, a method for the catalyzed addition of B�O s bonds to alkynes will be described. O-Heterocyclic boronic acid derivatives can be produced using this transformation, which is mild and exhibits broad functional group compatibility. The scope and mechanism of the alkoxyboration reaction will be discussed.

Alkoxyboration: Addition of B-O s bonds across alkynes

247th National Meeting (2014)

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