Organoboranes are extensively used in organic synthesis. Two noteworthy examples of organoborane chemistry include the hydroboration-oxidation reaction commonly studied in sophomore organic chemistry courses and the Nobel Prize winning Suzuki cross-coupling reaction. Catecholborane is a common boron source in the hydroboration reaction. However, the use of catecholborane is not ideal. For example, catechol is sensitive to oxidation and the catecholborane product can decompose upon exposure to air or moisture. Pinacolborane is a more stable alternative to catecholborane. Although the increased stability of pinacolborane also lessens its reactivity in hydroboration reactions. For example, only trace hydroboration products were observed in the reaction of phenylacetylene with pinacolborane after 7 h in refluxing THF. We have found that 9-borobicyclo[3.3.1]nonane (9-BBN) can be used to catalyze this hydroboration reaction. We present our study of the optimization of the 9-BBN catalyzed hydroboration reaction of phenylacetylene with pinacolborane.

9-BBN catalyzed hydroboration of phenylacetylene with pinacolborane

2019 Fall National Meeting

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