38151-26-7

Usage

Type of compound

Boron-containing heterocycle

Usage

Chiral catalyst in organic synthesis

Structure

Unique structure that allows effective catalysis

Reactions catalyzed

Asymmetric reduction and carbon-carbon bond formation

Applications

Production of pharmaceuticals, agrochemicals, and other fine chemicals

Importance

Valuable tool in chemical synthesis

Potential

Great potential for further applications in the future

InChI:InChI=1/C4H11BN2/c1-6-3-4-7(2)5-6/h5H,3-4H2,1-2H3

Upstream product

• 1380073-94-8 C₄H₁₅BN₂ 
• 16940-66-2 sodium tetrahydroborate 
• 110-70-3 N,N`-dimethylethylenediamine 

Relevant academic research and scientific papers

Catalytic Dehydrogenation of (Di)Amine-Boranes with a Geometrically Constrained Phosphine-Borane Lewis Pair

The o-phenylene bridged phosphine-borane iPr2P(o-C6H4)B(Fxyl)2 2 was prepared. Despite ring strain, it adopts a closed form, as substantiated by NMR, XRD, and DFT analyses. However, the corresponding open form i

Dehydrogenation of (Di)amine-Boranes by Highly Active Scandocene Alkyl Catalysts

The scandocene alkyl complexes (C5Me5)2ScR (1, R = CH(SiMe3)2; 5, R = CH2SiMe3) were found to be highly active catalysts for the dehydrogenation of dimethylamine-borane (DMAB), e

A Highly Effective Ruthenium System for the Catalyzed Dehydrogenative Cyclization of Amine-Boranes to Cyclic Boranes under Mild Conditions

We recently disclosed a new ruthenium-catalyzed dehydrogenative cyclization process (CDC) of diamine-monoboranes leading to cyclic diaminoboranes. In the present study, the CDC reaction has been successfully extended to a larger number of diamine-monoboranes (4-7) and to one amine-borane alcohol precursor (8). The corresponding NB(H)N- and NB(H)O-containing cyclic diaminoboranes (12-15) and oxazaborolidine (16) were obtained in good to high yields. Multiple substitution patterns on the starting amine-borane substrates were evaluated and the reaction was also performed with chiral substrates. Efforts have been spent to understand the mechanism of the ruthenium CDC process. In addition to a computational approach, a strategy enabling the kinetic discrimination on successive events of the catalytic process leading to the formation of the NB(H)N linkage was performed on the six-carbon chain diamine-monoborane 21 and completed with a 15NNMR study. The long-life bis-σ-borane ruthenium intermediate 23 possessing a reactive NHMe ending was characterized in situ and proved to catalyze the dehydrogenative cyclization of 1, ascertaining that bis σ-borane ruthenium complexes are key intermediates in the CDC process. Mild-mannered cyclization: The ruthenium-catalyzed dehydrogenative cyclization (CDC) process has been investigated by using a variety of amine-borane substrates (see figure). The reaction leads to the formation of the corresponding NB(H)N- and NB(H)O-containing cyclic aminoboranes and involves the formation of a bis-σ-borane ruthenium intermediate complex.

Dehydrogenation of diamine-monoboranes to cyclic diaminoboranes: Efficient ruthenium-catalyzed dehydrogenative cyclization

Remote control: The title reaction is the first example of a catalyzed dehydrogenative cyclization (CDC) of diamine-monoboranes to give cyclic diaminoboranes. The cyclization reaction is strongly dependent on the nature of the substitution pattern at the remote amino group.