15754-54-8

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4101, 1951 DOI: 10.1021/ja01153a015

Upstream product

• 109-65-9 1-bromo-butane 
• 762-04-9 phosphonic acid diethyl ester 
• 109-72-8 n-butyllithium 
• 109-69-3 n-Butyl chloride 
• 693-03-8 n-butyl magnesium bromide 
• 762-04-9 Diethyl phosphonate 
• 693-04-9 butyl magnesium bromide 
• 1732-72-5 di-n-butylphosphine 
• 75271-90-8 dibutylphosphinous iodide 
• 56660-55-0 ethyl ester of dibutyl phosphinic acid 

Downstream Products

• 61748-82-1 1-{Butyl-[2-(dibutyl-phosphinoylmethoxy)-ethoxymethyl]-phosphinoyl}-butane 
• 58046-14-3 1-Cyanoaethyl-dibutylphosphinat 
• 58046-13-2 Dibutyl-phosphinic acid 2-(dibutyl-phosphinoyl)-2-imino-1-methyl-ethyl ester 
• 26214-19-7 4-Chlor-α-dibutylphosphinyl-benzylalkohol 
• 26214-18-6 4-Brom-α-dibutylphosphinyl-benzylalkohol 
• 814-29-9 Tributylphosphine oxide 
• 1439386-07-8 C₁₃H₃₀NO₃P 
• 3492-32-8 dibutyl(difluoromethyl)phosphine oxide 
• 10557-66-1 dibutyl phenyl phosphate 
• 4141-63-3 1,2-Bis-(dibutyl-phosphino-oxid)-ethan 
• 4042-81-3 (benzyl)dibutylphosphine oxide 
• 145293-07-8 N-benzyl-aminomethyl-di(n-butyl)phosphine oxide 

Relevant academic research and scientific papers

Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds

We report a diaryldiselenide catalyst for cross-dehydrogenative nucleophilic functionalization of hydrophosphoryl compounds. The proposed organocatalytic cycle closely resembles the mechanism of the Atherton-Todd reaction, with the catalyst serving as a recyclable analogue of the halogenating agent employed in the named reaction. Phosphorus and selenium NMR studies reveal the existence of a P-Se bond intermediate, and structural analyses indicate a stereospecific reaction.

Silver-promoted cascade radical cyclization of γ,δ-unsaturated oxime esters with P(O)H compounds: synthesis of phosphorylated pyrrolines

A cascade radical cyclization was realized for the first silver-promoted imino-phosphorylation of γ,δ-unsaturated oxime esters, which provided a step-economical and redox-neutral route to access a variety of phosphorylated pyrrolines in good to excellent yields. Moreover, a new bulky trivalent phosphine ligand with a pyrroline motif was obtained through a deoxidation process.

Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides

Elemental phosphorus (red or white) reacts with alkyl bromides at 60–62 °C in the phase-transfer catalytic system KOH/H2O/PhMe/Et3BnNCl to afford alkyl-H-phosphinic acids in up to 47% yield.

Room temperature alkynylation of H-phosphi(na)tes and secondary phosphine oxides with ethynylbenziodoxolone (EBX) reagents

Highly efficient protocols for the alkynylation of H-phosphi(na)tes and secondary phosphine oxides with silyl, aryl and alkyl ethynyl-benziodoxolone (EBX) reagents are reported. Alkynyl phosphorus compounds were obtained in 69-93% yield without the need for a transition metal catalyst at room temperature under open flask conditions.

A "green" variation of the Hirao reaction: The P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates and secondary phosphine oxides with bromoarenes using a P-ligand-free Pd(OAc)2 catalyst under microwave and solvent-free conditions

The P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates, diphenylphosphine oxide and dialkylphosphine oxides with bromoarenes may be performed in the presence of a P-ligand-free Pd(OAc)2 catalyst and triethylamine under microwave-assisted (MW) and, in almost all cases, solvent-free conditions to afford diethyl arylphosphonates, alkyl diphenylphosphinates, aryldiphenylphosphine oxides and dialkylphenylphosphine oxides, respectively. This is the "greenest" accomplishment of the well-known Hirao reaction that has now been found to have general application for a broad spectrum of >P(O)H species with different reactivity and a great variety of substituted bromobenzenes. The alkyl phenyl-H-phosphinates were prepared by the MW-promoted alkylation of phenyl-H-phosphinic acid in the absence of any solvent. This journal is the Partner Organisations 2014.

Synthesis of gem-difluorocyclopropa(e)nes and O-, S-, N-, and P-difluoromethylated compounds with TMSCF2Br

Two-in-one: Me3SiCF2Br is an efficient difluorocarbene source and is compatible with both neutral and aqueous basic conditions. Bromide-ion-initiated [2+1] cycloaddition with alkenes/alkynes and hydroxide ion promoted α-addition with (thio)phenols, (thio)alcohols, sulfinates, heterocyclic amines, and H-phosphine oxides give the corresponding gem-difluorinated compounds with broad functional-group tolerance. Copyright

A superior method for the reduction of secondary phosphine oxides

(Chemical Equation Presented) Diisobutylaluminum hydride (DIBAL-H) and triisobutylaluminum have been found to be outstanding reductants for secondary phosphine oxides (SPOs). All classes of SPOs can be readily reduced, including diaryl, arylalkyl, and dialkyl members. Many SPOs can now be reduced at cryogenic temperatures, and conditions for preservation of reducible functional groups have been found. Even the most electron-rich and sterically hindered phosphine oxides can be reduced in a few hours at 50-70°C. This new reduction has distinct advantages over existing technologies.

Synthesis of new imidazole aminophosphine oxides

A series of imidazole aminophosphine oxides were synthesized by addition of dialkyl, diaryl, or alkyl(aryl)phosphine oxides to imidazole imines, formed from 1-benzylimidazole-5-carboxaldehyde and primary amines. The phosphine oxides were obtained by alkylation of diethyl phosphite, or ethyl phenylphosphinate with Grignard reagents. The new imidazole aminophosphine oxides were characterized by means of 1H and 31P NMR spectroscopy.

Radical deoxygenation of alcohols via their S-methyl dithiocarbonate derivatives with di-n-butylphosphine oxide as hydrogen atom donor

Various S-methyl dithiocarbonates of tertiary and secondary alcohols are readily deoxygenated in high isolated yields by radical deoxygenation with di-n-butylphosphine oxide and various radical initiators in boiling dioxane. Primary alcohols react similarly in boiling xylenes.

Aryl phosphinites

Aryl phosphinites of the formula (I) STR1 can be prepared in a simple manner and in high yields by reacting 2,4-di-tert.-butylphenylphosphonous dihalides with alkyl- or arylmagnesium bromides or alkyl- or arylmagnesium chlorides. Aryl phosphinites serve for the preparation of secondary phosphine oxides which are used as starting materials for the preparation of phosphine ligands in catalyst systems.