41593-58-2

Usage

Uses

Used in Organic Chemistry:
BORANE-DIPHENYLPHOSPHINE COMPLEX is used as a reactant for nucleophilic addition reactions, where it acts as an anion to facilitate the process. This application is crucial for the synthesis of various organic compounds and contributes to the development of new materials and pharmaceuticals.
Used in Catalytic Dehydrogenation:
In the presence of ruthenium bidentate phosphine complexes, BORANE-DIPHENYLPHOSPHINE COMPLEX is used as a catalyst for dehydrogenation reactions. This application is essential in the production of various chemicals and materials, as well as in the synthesis of pharmaceuticals.
Used in Deprotonation Reactions:
BORANE-DIPHENYLPHOSPHINE COMPLEX serves as a reagent in deprotonation reactions, where it helps to remove a proton (H+) from a molecule. This process is vital in the synthesis of various organic compounds and contributes to the development of new materials and pharmaceuticals.
Used in Catalytic Coupling with Alkynyl Bromides:
BORANE-DIPHENYLPHOSPHINE COMPLEX is used as a catalyst in the coupling reactions with alkynyl bromides, leading to the formation of new carbon-carbon bonds. This application is crucial in the synthesis of complex organic molecules and the development of new materials and pharmaceuticals.
Used in Catalyst-free Staudinger Ligation:
For indirect 18F-radiolabeling, BORANE-DIPHENYLPHOSPHINE COMPLEX is used in a catalyst-free Staudinger ligation process. This application is significant in the field of medical imaging, as it allows for the development of radiolabeled compounds that can be used in diagnostic procedures.
Used in the Preparation of Chiral Phosphine-Phosphite Bidentate Ligands:
BORANE-DIPHENYLPHOSPHINE COMPLEX is utilized in the preparation of chiral phosphine-phosphite bidentate ligands with a biphenyl backbone. These ligands are essential in asymmetric catalysis, which is a crucial process in the synthesis of enantiomerically pure compounds, often found in pharmaceuticals.
Used in Reactions with Frustrated Lewis Pair Combinations:
BORANE-DIPHENYLPHOSPHINE COMPLEX is used in reactions involving frustrated Lewis pair combinations of group 14 triflates and sterically hindered nitrogen bases. This application is significant in the development of new catalytic systems and the synthesis of various organic compounds.

Upstream product

• 829-85-6 diphenylphosphane 
• 4559-70-0 Diphenylphosphine oxide 
• 13292-87-0 dimethylsulfide borane complex 
• 1079-66-9 chloro-diphenylphosphine 
• 108-86-1 bromobenzene 
• 1707-03-5 diphenyl-phosphinic acid 
• 10043-11-5 borane-ammonia complex 
• 719-80-2 Ethyl diphenylphosphinite 
• 1733-55-7 ethyl diphenylphosphinate 
• 14044-65-6 borane-THF 
• 106-40-1 4-bromo-aniline 
• 22859-57-0 N,N-diisopropyl-1,1-diphenylphosphanamine 
• 16940-66-2 sodium tetrahydroborate 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 16557-29-2 (Diphenylphosphino)borane 
• 76144-87-1 (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) 
• 127686-85-5 (C₆H₅)2P(BH₃)CH₂CH₂CO₂C₂H₅ 
• 127686-71-9 (C₆H₅)2P(BH₃)CH₂CO₂CH₃ 
• 127686-83-3 (C₆H₅)2P(BH₃)C(OH)(CH₃)2 
• 127686-90-2 diphenylcyclohexylphosphine-borane complex 
• 127686-75-3 allyl(diphenyl)phosphine-borane 
• 127686-79-7 (C₆H₅)2P(BH₃)CH₂COCH₃ 
• 127686-89-9 Ph₂P(BH₃)CH₂CMe=CMe₂ 
• 127709-43-7 diphenyl(3-hydroxypropyl)phosphine borane 
• 127686-87-7 (C₆H₅)2P(BH₃)CH₂CH₂CN 
• 127686-78-6 diphenyl(methoxymethyl)phosphine-borane complex 
• 127686-76-4 diphenyl(n-butyl)phosphine-borane 
• 97764-52-8 Ph₂P(BH₃)CH(OH)C₆H₄Cl-p 

Relevant academic research and scientific papers

Ni-Catalyzed enantioselective reductive arylcyanation/cyclization of: N -(2-iodo-aryl) acrylamide

A Ni/(S,S)-BDPP-catalyzed intramolecular Heck cyclization of N-(2-iodo-aryl) acrylamide with 2-methyl-2-phenylmalononitrile was developed to give oxindoles with good enantioselectivities. We found that utilizing such an electrophilic cyanation reagent cou

Direct conversion of sec-phosphine oxides to sec-phosphine-boranes using BH3

An effective and mild synthetic method for secondary phosphine-boranes from secondary phosphine oxides was developed. The slow addition of borane-tetrahydrofuran to a solution of secondary phosphine oxides at ambient temperature gave secondary phosphine-boranes with high yield. The use of air-sensitive secondary phosphines, which are common substrates for secondary phosphine-borane syntheses, is avoided in this mild process. Moreover, generation of by-products, such as secondary hydroxy-phosphine-boranes, is also minimized.

The Trityl-Cation Mediated Phosphine Oxides Reduction

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

Activation of sodium borohydride via carbonyl reduction for the synthesis of amine- And phosphine-boranes

A highly versatile synthesis of amine-boranes via carbonyl reduction by sodium borohydride is described. Unlike the prior bicarbonate-mediated protocol, which proceeds via a salt metathesis reaction, the carbon dioxide-mediated synthesis proceeds via reduction to a monoformatoborohydride intermediate. This has been verified by spectroscopic analysis, and by using aldehydes and ketones as the carbonyl source for the activation of sodium borohydride. This process has been used to produce borane complexes with 1°-, 2°-, and 3°-amines, including those with borane reactive functionalities, heteroarylamines, and a series of phosphines.

Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes

A general approach to various α-phosphorus-substituted oximes (β-oximinoalkyl-substituted phosphonates, phosphine oxides, phosphine-borane complexes, and phosphonium salts) was developed. The strategy exploits hitherto unknown Michael addition of PH-containing compounds (diphenylphosphine oxide, diisopropyl phosphite, phosphine-borane complexes, and triphenylphosphonium bromide) to unstable conjugated nitrosoalkenes, which are generated in situ from corresponding nitrosoacetals. The resulting α-phosphorus-substituted oximes can be considered as useful P-, N-, and O-ligands for catalysis and precursors to valuable β-aminophosphonates.

Exploring the Reactivity of Donor-Stabilized Phosphenium Cations: Lewis Acid-Catalyzed Reduction of Chlorophosphanes by Silanes

Phosphane-stabilized phosphenium cations react with silanes to effect either reduction to primary or secondary phosphanes, or formation of P-P bonded species depending upon counteranion. This operates for in situ generated phosphenium cations, allowing catalytic reduction of P(III)-Cl bonds in the absence of strong reducing agents. Anion and substituent dependence studies have allowed insight into the competing mechanisms involved.

Reduction of Tertiary Phosphine Oxides by BH 3 Assisted by Neighboring Activating Groups

Tertiary sulfanylphosphine and aminoalkylphosphine oxides can be easily converted into the corresponding tertiary sulfanylphosphine- and aminoalkylphosphine-boranes, respectively, through the facile P=O bond reduction by borane complexes. The easy reduction of the strong P=O bond by BH 3, a mild reducing agent, has been achieved through an intramolecular P=O - B complexation directed by proximal SH or NH activating groups located at the α- or β-position to the P=O bond. A generalized reduction mechanism has been proposed.

A Versatile Approach for Site-Specific Lysine Acylation in Proteins

Using amber suppression in coordination with a mutant pyrrolysyl-tRNA synthetase-tRNAPylpair, azidonorleucine is genetically encoded in E. coli. Its genetic incorporation followed by traceless Staudinger ligation with a phosphinothioester allows the convenient synthesis of a protein with a site-specifically installed lysine acylation. By simply changing the phosphinothioester identity, any lysine acylation type could be introduced. Using this approach, we demonstrated that both lysine acetylation and lysine succinylation can be installed selectively in ubiquitin and synthesized histone H3 with succinylation at its K4 position (H3K4su). Using an H3K4su-H4 tetramer as a substrate, we further confirmed that Sirt5 is an active histone desuccinylase. Lysine succinylation is a recently identified post-translational modification. The reported technique makes it possible to explicate regulatory functions of this modification in proteins.

Intramolecular nucleophilic substitution of ω-haloalkylphosphine derivatives

ω-Haloalkylphosphine derivatives undergo the intramolecular nucleophilic substitution reaction upon treatment with a strong base, yielding either cycloalkylphosphine derivatives or heterocyclic phosphine derivatives. The selectivity of the cyclization of

Phosphine- and amine-borane dehydrocoupling using a three-coordinate iron(II) β-diketiminate precatalyst

Dehydrocoupling of phosphine- and amine-boranes is reported using an iron(II) β-diketiminate complex. Dehydrocoupling of amine-boranes is far more facile than the phosphine counterpart, the former proceeding at room temperature with 1 mol% iron precatalys