This work describes oxyboration—the addition of B–O σ bonds to C–C π bonds— to form borylated heterocycles. This type of transformation provides a simple and efficient route to potential building blocks for drug discovery. This oxyboration reaction is mild and tolerant of a wide range of functional groups that are incompatible with alternative technologies. Mechanistic experiments suggest an activation pathway employing a carbophilic Lewis acidic/Lewis basic catalyst that could simultaneously activate both the C–C π bonds and the B–O σ bond partners to allow for the <i>anti</i> addition. The reaction is scalable and the complimentary bond disconnections enabled by this method are highlighted in the synthesis of valdecoxib, a COX-2 inhibitor and its analog.<br/>

Oxyboration: Addition of B-O sigma bonds to C-C pi bonds

251st National Meeting (2016)

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