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Borane-Trimethylamine Complex: A Versatile Reagent in Organic Synthesis

Dario Perdicchia¹

¹Dipartimento di Chimica, Università Degli Studi di Milano, Via Golgi 19, 20133 Milan, Italy.

Molecules (Basel, Switzerland)

|May 11, 2024

Abstract:

Borane-trimethylamine complex (Me₃N·BH₃; BTM) is the most stable of the amine-borane complexes that are commercially available, and it is cost-effective. It is a valuable reagent in organic chemistry with applications in the reduction of carbonyl groups and carbon-nitrogen double bond reduction, with considerable examples in the reduction of oximes, hydrazones and azines. The transfer hydrogenation of aromatic N-heterocycles and the selective N-monomethylation of primary anilines are further examples of recent applications, whereas the reduction of nitrobenzenes to anilines and the reductive deprotection of N-tritylamines are useful tools in the organic synthesis. Moreover, BTM is the main reagent in the regioselective cleavage of cyclic acetals, a reaction of great importance for carbohydrate chemistry. Recent innovative applications of BTM, such as CO₂ utilization as feedstock and radical chemistry by photocatalysis, have extended their usefulness in new reactions. The present review is focused on the applications of borane-trimethylamine complex as a reagent in organic synthesis and has not been covered in previous reviews regarding amine-borane complexes.

Keywords:

amine–borane complexes borane ionic hydrogenation radical reactions reduction

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