Hazardous Chemistry: Borane Chemistry and Organoboranes Chemistry

At Novasep, we produce diborane gas (B₂H₆) for the preparation of various borane reagents or to be used directly in several reactions such in several reactions such as reduction, hydroboration, and many other regioselective and stereoselective reactions.

Diborane

Due to its high sensitivity to air and moisture, as well as its high toxicity and explosiveness, using diborane requires special procedures and equipment that perfectly match Novasep’s expertise and capabilities.

Rather than preparing borane in solution, we handle gaseous diborane in situ in order to have higher conversion rates, leading to high reaction yields and great productivity. Moreover, only a small amount of solvent is necessary, leading to greener reactions.  For example, generating 20 kg of diborane gas eliminates the need to use 1500 L of a 1M BH3:THF solution.

We are equipped with a 1000 L reactor dedicated for the production of about 10 tons per year of diborane.
Produced diborane gas (B₂H₆) can be used directly for the reaction or can be transformed into various borane agents for special needs in terms of reactivity and selectivity such as 9-BBN, catecholborane, Diisopinocamphenylborane (iPc)₂BH, Sia₂BH, Corey borolidine, alpine borane, etc.

For specific applications, we can prepare complexes of borane with a Lewis base such as THF, dimethylsulfide, morpholine, thioxane, pyridine, amine, phosphine, etc.

Reduction using boron hydrides

Boron hydrides offer interesting applications in the reduction of various functional groups and are commonly used from kilogram to ton scale by Novasep.

Both racemic and asymmetric versions are performed in our facilities. One of the most famous enantioselective boron hydride reductions is the oxazaborolidine-catalyzed asymmetric reduction of ketones named Corey-Bakshi-Shibata (CBS) reduction. For this reaction, we produce the CBS catalyst in house starting with chiral diphenylprolinol.

Hydroboration of alkenes with diborane

Diborane is a versatile reagent for the stereospecific (anti-Markovnikov) addition of functional groups to olefins via hydroboration.

As for boron hydride reduction, both  racemic and asymmetric versions of hydroboration are performed at Novasep

Chemistry of borane and organoborane compounds

In addition to reduction and hydroboration reactions, we have great expertise in most of the aspects of borane and organoborane chemistry, for example:

1. Reactions of allyl and crotyl boranes with aldehyde, thanks to our capabilities for cryogenic reactions, using racemic or chiral boranes
2. Preparation of starting material for Suzuki cross-coupling reaction
3. Addition of hindered organoborane on alkyne to form the corresponding alkene
4. Boron enolate chemistry, thanks to our capabilities for cryogenic reactions

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