131765-96-3

Usage

Uses

Used in Organic Chemistry:
Dicyclohexylamine borane complex is used as a borylation reagent for the conversion of aryl and vinyl halides into boronic acid derivatives. This application is particularly valuable due to its ability to perform the conversion in a single pot, simplifying the process and reducing the need for multiple steps.
The complex is effective in producing a variety of boronic acid derivatives, such as BF3K, Bpin, MIDA, and others, depending on the chosen quench and workup methods. This versatility makes dicyclohexylamine borane complex a valuable tool in the synthesis of various organic compounds and contributes to its widespread use in research and industrial applications.

Upstream product

• 16940-66-2 sodium tetrahydroborate 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 13292-87-0 dimethylsulfide borane complex 
• 74076-45-2 dicyclohexylamine; protonated form 
• 4693-92-9 dicyclohexylamine hydrochloride 
• 14044-65-6 borane-THF 

Downstream Products

• 260432-80-2 [((C₆H₁₁)2N)BH₂]2 
• 1333-74-0 hydrogen 
• 145240-28-4 4-butylphenylboronic acid 
• 5720-07-0 4-methoxyphenylboronic acid 
• 32316-92-0 naphthalene-2-boronic acid 
• 13922-41-3 1-Naphthylboronic acid 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 1765-93-1 4-fluoroboronic acid 
• 98-80-6 phenylboronic acid 
• 22093-04-5 (dicyclohexylamino)borane 
• 22093-03-4 HB{N(c-C₆H₁₁)2}2 
• 1191993-40-4 [W(CO)5(η1-BH3NHCy2)] 

Relevant academic research and scientific papers

Non-biaryl atropisomerism at the C-B bond in sterically hindered aminoarylboranes

Sterically hindered aminoarylboranes featuring atropisomerism about the C-B bond were prepared by addition of organomagnesium species onto readily accessible dialkylamine-borane complexes. Some of these aminoarylboranes, isosteres of vinyl styrene derivatives, were resolved by HPLC on the chiral stationary phase. They are the first examples of a non-biaryl type system which display slow rotation about a C-B bond.

Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.

METHOD FOR PRODUCING STEREOSELECTIVE EPOXYKETONE COMPOUND

A novel method for producing a stereoselective epoxyketone compound is provided. A method for producing an epoxyketone compound represented by the formula (1), as represented by the following scheme, whereby it is possible to obtain an epoxyketone derivative in good yield and at high selectivity and to provide an industrially useful production method and an intermediate thereof. wherein R1 is a hydrogen atom, a linear, branched or cyclic alkyl group, an aromatic group which may have a substituent, or a heterocyclic group which may have a substituent, and R2 is a protective group for an amino group. R is a hydrogen atom or a C1-10 alkyl group, and R's may be the same or different, provided that at least one R is a C1-10 alkyl group.

Dehydrocoupling reactions of borane-secondary and -primary amine adducts catalyzed by group-6 carbonyl complexes: Formation of aminoboranes and borazines

Photoirradiation of a solution of BH3·NHR2 (1a: R = Me, 1b: R = 1/2C4H8, 1c: R = 1/2C 5H10, 1f: R = Et) containing a catalytic amount of a group-6 metal carbonyl complex, [M(CO)6] (M = Cr, Mo, W), led to dehydrogenative B-N covalent bond formation to produce aminoborane dimers, [BH2NR2]2 (2a-c, f), in high yield. During these reactions a borane σ complex, [M(CO)5(η1- BH3·NHR2)] (3), was detected by NMR spectroscopy. Similar catalytic dehydrogenation of bulkier amineboranes, BH 3·NHiPr2 (1d) and BH3· NHCy2 (1e, Cy = cyclo-C6H11), afforded monomeric products BH2=NR2 (4d, e). The reaction mechanism of the dehydrocoupling was investigated by DFT calculations. On the basis of the computational study, we propose that the catalytic dehydrogenation reactions proceed via an intramolecular pathway and that the active catalyst is [Cr(CO)4]. The reaction follows a stepwise mechanism involving NH and BH activation. Dehydrocoupling of borane-primary amine adducts BH 3·NH2R (1g: R = Me, 1h: R = Et, 1i: R = tBu) gave borazine derivatives [BHNR]3 (5g-i).

When is a nanoparticle a cluster? An operando EXAFS study of amine borane dehydrocoupling by Rh4-6 clusters

X-ray absorption fine structure (XAFS) is used to determine the structure of the rhodium cluster present during the catalyzed dehydrocoupling of amine boranes under operando conditions. We show how a variety of XAFS strategies can be used in combination with other analytical methods to differentiate homogeneous from heterogeneous systems. Analysis of the in situ XAFS spectra using a series of amine boranes (NH3BH3, R 2NHBH3, and RNH2BH3 where R = methyl, isopropyl, tert-butyl, and cyclohexyl) and rhodium catalyst precursor compounds (including chloro-(1,5-cyclooctadiene)rhodium (I) dimer, bis(1,5-cyclooctadiene)rhodium (I) trifluoromethanesulfonate, chlorodicarbonylrhodium (I) dimer, dichloro(pentamethylcylcopentadienyl)rhodium (III) dimer, hexarhodium hexadecacarbonyl, and tetrarhodium dodecacarbonyl) strongly suggest that the active catalyst species for this reaction is a homogeneous rhodium complex. Rhodium clusters containing four or six rhodium atoms (Rh4-6) bound to amine boranes are observed as the major (>99%) rhodium containing species during and after the catalyzed anaerobic dehydrocoupling. During the later stages of the reaction a nonmetallic rhodium complex precipitates in which individual Rh4-6 clusters likely form polymer chains ligated by the reaction products that have two or more ligating sites. The best fits of the XAFS data, using ab initio calculations of FEFF theory, show that the major rhodium species (80%) has each rhodium atom directly bound to three rhodium atoms with an observed bond distance of 2.73 A and to two boron atoms at 2.10 A. A minor (20%) rhodium species has each rhodium atom bound to four rhodium atoms with a bond distance of about 2.73 A and a single rhodium atom at a nonbonding distance of 3.88 A. No metallic rhodium was observed at any time during the anaerobic reaction.

(Aryl)(amino) borane compounds, method for preparing same

The invention concerns (aryl)(amino)borane compounds and a method for preparing same. Said compounds are of formula A-BH-NR1R2, wherein: R1 and R2 are selected among linear, branched or cyclic alkyl radicals, an

Reduction of steroidal ketones with amine - Boranes

Complexes of secondary amines with borane, R2NH·BH 3, surpass sodium borohydride as reducing agents for saturated and unsaturated steroidal 3-, 12-, 17-, and 20-ketones as regards chemo- and regioselectivity and mildness of the reaction conditions. In the case of 12-ketones, stereoselectivity is also improved.