Open-Flask Hydroboration of Alkenes Using Ammonia Borane

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Current methods for hydroboration utilize pyrophoric, moisture-sensitive reagents that pose a safety risk. The reactions are usually performed under strict anhydrous conditions, avoiding contact with air and moisture. Amine-boranes are stable borane complexes, but very few are used for hydroboration.

Researchers at Purdue University have developed a method for achieving hydroboration of alkenes using ammonia borane. This is the first open-to-air hydroboration protocol using air- and moisture-stable reagents without the need for inert conditions or metal catalysts. Moreover, this process can uniquely produce the hydroboration products, ammonia-trialkylboranes, and aminodialkylboranes. This method increases the utility of hydroboration, providing opportunity for new discoveries.

-Safer than traditional hydroboration
-Open-flask hydroboration
-Access to ammonia-trialkylboranes and aminodialkylboranes
-Hydroboration-oxidation sequence provides corresponding alcohols in high yields
-High boron content and air- and moisture-stable reagent

Potential Applications:
-Organic synthesis
-Industrial chemistry
-Chemical education
Aug 18, 2017
Utility Patent
United States
Aug 20, 2019

Aug 19, 2016
United States
Purdue Office of Technology Commercialization
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