4856-92-2

Upstream product

• 16940-66-2 sodium tetrahydroborate 
• 109-63-7 trifluoroborane diethyl ether 
• 100-46-9 benzylamine 
• 3287-99-8 benzylamine hydrochloride 
• 14044-65-6 borane-THF 
• 100-47-0 benzonitrile 

Downstream Products

• 11113-50-1 boric acid 
• 55124-36-2 dibenzylamine borane 
• 854204-41-4 N,N-propylbenzylamine borane 
• 854204-51-6 N,N,N-dipropylbenzylamine borane 
• 331282-35-0 N,N-butylbenzylamine borane 
• 854204-53-8 N,N,N-dibutylbenzylamine borane 
• 1452577-11-5 C₁₄H₂₄B₃N₂^(1-)*Na⁽¹⁺⁾ 
• 1485-70-7 N-benzylbenzamide 
• 35665-26-0 N-benzylcyclohexanecarboxamide 
• 6283-98-3 N-benzylhexanamide 
• 26209-45-0 N-benzyl-2,2-dimethylpropanamide 
• 588-46-5 N-(phenylmethyl)acetamide 
• 7387-69-1 N-benzyl-2,2,2-trifluoroacetamide 
• 6343-54-0 N-benzylformamide 

Relevant academic research and scientific papers

AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS

The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.

Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions

A simple and efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine-BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to 95%. The strategy was applied to the synthesis of 15N labeled in 89% yield.

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids

Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities allows for the preparation of functionalized amides. An intermolecular mechanism proceeding through a triacyloxyborane-amine complex is proposed.

Amine-boranes bearing borane-incompatible functionalities: Application to selective amine protection and surface functionalization

The first general open-flask synthesis of amine-boranes with inexpensive and readily available reagents, such as sodium borohydride, sodium bicarbonate, water, and the desired amines is described. Even amines bearing borane-reactive functionalities, such as alkene, alkyne, hydroxyl, thiol, ester, amide, nitrile, and nitro are well tolerated. Some of these novel amine-boranes represent stable molecules containing potentially incompatible electrophilic and nucleophilic centers in proximity. This convenient scalable synthesis provides a novel class of organic ligands for surface functionalization, as demonstrated by the formation of self-assembled layers of thiol- and alkoxysilane-bearing amine-boranes on gold and silica surfaces, respectively.

Water‐promoted, open‐flask synthesis of amine‐boranes: 2‐methylpyridine‐borane (2‐picoline‐borane)

A procedure yielding 2‐methylpyridine‐borane as a white solid is presented. Sodium borohydride and powdered sodium bicarbonate are added into a single‐necked, air‐dried round‐bottomed flask with a Teflon‐coated, egg‐shaped magnetic stir bar. A discussion on amine‐boranes, reductive amination with aldehyde bisulfites and carbohydrates, and metathesis of metal borohydrides with alkylammonium salts concludes the chapter.