Open-Flask Hydroboration of Alkenes Using Ammonia Borane
A novel, open-to-air hydroboration protocol uses stable reagents, eliminating safety risks and the need for inert conditions, while uniquely yielding valuable trialkylborane and aminodialkylborane products for organic synthesis and industrial chemistry.
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.
Advantages:
-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
TRL: 6
Intellectual Property:
Provisional-Patent, 2016-08-19, United States | Utility Patent, 2017-08-18, United States
Keywords: hydroboration, ammonia borane, open-to-air hydroboration, air-stable reagents, moisture-stable reagents, open-flask hydroboration, alkene hydroboration, amine-borane complexes, organic synthesis, industrial chemistry