56598-35-7

Upstream product

• 253185-03-4 tert-butylbenzene 
• 38442-51-2 tert-butylmercury chloride 
• 15475-27-1 potassium diphenylphosphine 
• 542-69-8 1-iodo-butane 
• 1079-66-9 chloro-diphenylphosphine 
• 109-69-3 n-Butyl chloride 
• 829-85-6 diphenylphosphane 
• 594-19-4 tert.-butyl lithium 
• 791-28-6 Triphenylphosphine oxide 
• 62485-00-1 isobutyl phosphorodichloridate 
• 71-43-2 benzene 
• 507-20-0 tertiary butyl chloride 
• 109-65-9 1-bromo-butane 
• 78-77-3 Isobutyl bromide 

Downstream Products

• 21955-54-4 Benzyl-diphenyl-t-butylphosphoniumbromid 
• 6002-34-2 tert-butyldiphenylphosphine 
• 21448-79-3 t-butylmethylphenylphosphine oxide 

Relevant academic research and scientific papers

Aryl group - A leaving group in arylphosphine oxides

The treatment of triphenylphosphine oxide with organometallic reagents leads to the substitution of up to three phenyl substituents with the incoming carbon nucleophile. The replacement of the phenyl/aryl group in tertiary diarylalkylphosphine oxides or even aryldialkylphosphine oxides was also observed. Naphthyl-substituted phosphine oxides undergo Michael-type addition at the naphthyl group when treated with organolithium reagent.

Efficient nickel-catalyzed phosphinylation of C-S bonds forming C-P bonds

The first nickel-catalyzed phosphinylation of C-S bonds forming C-P bonds is developed. This transformation can proceed readily with the simple Ni(cod)2 at a loading down to 0.1 mol% at the 10 mmol scale. A variety of aryl sulfur compounds, i.e. sulfides, sulfoxides and sulfones all couple with P(O)-H compounds to produce the corresponding organophosphorus compounds in high yields, which provides an efficient new method for the construction of C-P bonds.

Nickel-catalyzed phosphorylation of aryl triflates with P([Formula presented] compounds

A nickel-catalyzed phosphorylation of aryl triflates with P([Formula presented] compounds is disclosed. This reaction can proceed smoothly under a mild reaction condition, producing the corresponding aryl phosphorus compounds in good to high yields.

Nickel-Catalyzed Phosphorylation of Phenol Derivatives via C-O/P-H Cross-Coupling

An efficient nickel-catalyzed phosphorylation of phenol derivatives with P(O)-H compounds via C-O/P-H cross-coupling is described. Under the reaction conditions, various phenyl pivalates coupled readily with hydrogen phosphoryl compounds to afford the corresponding coupling products aryl phosphonates and aryl phosphine oxides in good to high yields.

Nickel-catalysed P-C bond formation via P-H/C-CN cross coupling reactions

Nickel-catalysed P-H/C-CN cross coupling reactions take place efficiently under mild reaction conditions affording the corresponding sp2C-P bonds. This transformation provides a convenient method for the preparation of arylphosphines and arylphosphine oxides from the readily available P-H compounds and arylnitriles. This journal is

Efficient copper(I)-catalyzed coupling of secondary phosphine oxides with aryl halides

A catalytic system has been developed for the efficient synthesis of tertiary arylphosphine oxides by coupling of readily available secondary phosphine oxides with aryl bromides or iodides in the presence of copper(I) iodide as a catalyst and (S)-α-phenylethylamine as a ligand. The system exhibits high activity in the coupling of secondary diaryl-, alkylaryl- and dialkylphosphine oxides.

Homolytic substitution at phosphorus for the synthesis of alkyl and aryl phosphanes

(Chemical Equation Presented) A transition-metal-free radical phosphonation using Me3SnPPh2 and the less toxic Me 3SiPPh2 is reported. These readily available reagents react highly efficiently with primary and secondary alkyl radicals. Moreover, aryl radicals and tertiary alkyl radicals are phosphonated with Me 3SnPPh2 (see scheme; R = aryl, alkyl, vinyl; X = 1, Br, OC(S)imidazolyl). DFT calculations provide insights into the mechanism of the reaction.

The endocyclic restriction test: Investigation of the geometries of nucleophilic substitution at phosphorus(III) and phosphorus(V)

Double labeling has been used under the endocyclic restriction test to show that transfers of phosphorus from oxygen to carbon in the conversions of lithio phosphinite 1 to alkoxy phosphine 8, of lithio phosphinite 2 to alkoxy phosphine 9, of lithio phosphinate 3 to alkoxy phosphine oxide 10, and of lithio phosphinite borane 4 to alkoxy phosphine borane 11 proceed in an intramolecular fashion. The transfers of stereogenic phosphorus in the conversions of lithio phosphinite (R)-5 to alkoxy phosphine (R)-12, of lithio phosphinate (S)-6 to alkoxy phosphine oxide (S)-13, and of lithio phosphinite borane (R)-7 to alkoxy phosphine borane (R)-14 proceed with retention of stereochemistry at phosphorus. These results rule out the classic in-line S(N)2 pathway and the geometrically equivalent in-line addition-elimination pathway for these endocyclic transfers of phosphorus. The most likely pathway for these nucleophilic substitutions at phosphorus is initial apical nucleophilic attack followed by pseudorotation and elimination of the apical alkoxy leaving group.