61157-16-2

Upstream product

• 3437-95-4 2-Iodothiophene 
• 17154-34-6 (trimethylsilyl)diphenylphosphine 
• 96-43-5 2-thienyl chloride 
• 1079-66-9 chloro-diphenylphosphine 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 829-85-6 diphenylphosphane 
• 1003-09-4 2-bromothiophene 
• 603-35-0 triphenylphosphine 
• 188290-36-0 thiophene 
• 40841-62-1 (diphenylphosphino)(p-tolyl)methanone 
• 4376-01-6 sodium diphenylphosphide 
• 1031-93-2 diphenyl(p-tolyl)phosphine 
• 7650-91-1 benzyldiphenylphosphane 
• 6002-34-2 tert-butyldiphenylphosphine 

Downstream Products

• 79133-89-4 diphenyl (2-thienyl)phosphine selenide 
• 588-59-0 stilbene 
• 81380-87-2 dichloro-bis(diphenyl(2-thienyl)phosphine)platinum(II) 
• 199432-52-5 dichloro-bis(diphenyl(2-thienyl)phosphine)palladium(II) 
• 93708-73-7 RhCl(CO)2((C₆H₅)2PC₄H₃S)2 
• 107087-71-8 [Rh((C₆H₅)2P(SC₄H₃))2(C₈H₁₂)]⁽¹⁺⁾*BF₄^(1-)=[Rh((C₆H₅)2P(SC₄H₃))2(C₈H₁₂)]BF₄ 
• 221878-39-3 Co3(μ3-CMe)(CO)7(diphenyl-2-thienylphosphine)2 
• 221878-37-1 Co3(μ3-CMe)(CO)8(diphenyl-2-thienylphosphine) 
• 226255-45-4 Mn₂(CO)9(P(C₆H₅)2(C₄H₃S)) 
• 226255-48-7 Re₂(CO)8(P(C₆H₅)2(C₄H₃S)) 

Relevant academic research and scientific papers

Ready Approach to Organophosphines from ArCl via Selective Cleavage of C-P Bonds by Sodium

The preparation, application, and reaction mechanism of sodium phosphide R2PNa and other alkali metal phosphides R2PM (M = Li and K) have been studied. R2PNa could be prepared, accurately and selectively, via the reactions of SD (sodium finely dispersed in mineral oil) with phosphinites R2POR′ and chlorophosphines R2PCl. R2PNa could also be prepared from triarylphosphines and diarylphosphines via the selective cleavage of C-P bonds. Na was superior to Li and K for these reactions. R2PNa reacted with a variety of ArCl to efficiently produce R2PAr. ArCl is superior to ArBr and ArI since they only gave low yields of the products. In addition, Ph2PNa is superior to Ph2PLi and Ph2PK since Ph2PLi did not produce the coupling product with PhCl, while Ph2PK only gave a low yield of the product. An electron-withdrawing group on the benzene ring of ArCl greatly accelerated the reactions with R2PNa, while an alkyl group reduced the reactivity. Vinyl chloride and alkyl chlorides RCl also reacted efficiently. While t-BuCl did not produce the corresponding product, admantyl halides could give the corresponding phosphine in high yields. A wide range of phosphines were prepared by this method from the corresponding chlorides. Unsymmetric phosphines could also be conveniently generated in one pot starting from Ph3P. Chiral phosphines were also obtained in good yields from the reactions of menthyl chlorides with R2PNa. Possible mechanistic pathways were given for the reductive cleavage of R3P by sodium generating R2PNa and the substitution reactions of R2PNa with ArCl generating R2PAr.

A practical synthesis of unsymmetrical triarylphosphines by heterogeneous palladium(0)-catalyzed cross-coupling of aryl iodides with diphenylphosphine

The heterogeneous cross-coupling reaction of aryl iodides with diphenylphosphine was achieved in DMAc at 130 °C in the presence of 1.0 mol% of MCM-41-supported tridentate nitrogen palladium(0) complex [MCM-41-3N-Pd(0)] with KOAc as base, yielding a variety of unsymmetrical triarylphosphines in good to excellent yields. The turnover frequency (TOF) of the catalyst can reach 30.67 h?1. This new heterogeneous palladium(0) catalyst could easily be prepared by a simple procedure from commercially readily available reagents, and exhibited the same catalytic activity as homogeneous Pd(OAc)2 or Pd(PPh3)4, and could be recovered by filtration of the reaction solution and recycled at least seven times without significant loss of catalytic activity.

An efficient heterogeneous cross-coupling of aryl iodides with diphenylphosphine catalyzed by copper (I) immobilized in MCM-41

The heterogeneous cross-coupling reaction of aryl iodides with diphenylphosphine was achieved in toluene at 115?°C in the presence of 10?mol% of phenanthroline-functionalized MCM-41-supported copper (I) complex (Phen-MCM-41-CuI) with Cs2CO3 as base, yielding various unsymmetric triarylphosphines in good to excellent yields. This protocol can tolerate a wide range of functional groups and does not need the use of expensive additives or harsh reaction conditions. This heterogeneous Cu (I) catalyst exhibited the same catalytic activity as homogeneous CuI/Phen system, and could easily be recovered by a simple filtration of the reaction solution and recycled up to seven times without significant loss of activity.

Palladium-catalyzed C–P(III) bond formation reaction with acylphosphines as phosphorus source

Palladium-catalyzed C–P(III) bond formation reaction employing acylphosphines as the phosphorus source was developed. Under the optimized conditions, acylphosphines could react with aryl halides directly affording trivalent phosphines in up to 94% yield.

Ligand-free palladium catalyzed phosphorylation of aryl iodides

A reusable ligand-free palladium catalyzed phosphorylation of aryl iodides using PdCl2/tetrabutylammonium bromide is described. Functionalized triarylphosphines were obtained in good to excellent yields in the absence of external reductants and supporting ligands.

Spectroscopic study of phosphine-substituted oligothiophenes

The spectroscopic behavior (solution and solid-state absorption and emission) of a series of mono(diphenylphosphino) and bis-(diphenylphosphino) ?±-substituted oligothiophenes varying in length from one to three thienyl rings is described. The absorption

Application of palladium-catalyzed Pd-aryl/P-aryl exchanges: Preparation of functionalized aryl phosphines by phosphination of aryl bromides using triarylphosphines

Palladium-catalyzed Pd-aryl/P-aryl interchange reaction was applied in the synthesis of various functionalized arylphosphines. This phosphination used inexpensive, readily available and air stable triarylphosphines as the phosphinating agents. Broad functional groups were compatible including keto, aldehyde, ester, nitrile, ether, chloride, pyridyl and thiophenyl groups. Halides were found to be good promoter for the rates and yields of the reaction.

Copper-catalyzed synthesis of unsymmetrical triarylphosphines

Various triarylphosphines have been prepared by coupling diphenylphosphine with aryl iodides with catalytic amounts of CuI in the presence of either K2CO3 or CS2CO3, in good yields. This method can tolerate a variety of functional groups and does not require the use of expensive additives, or harsh reaction conditions, and is palladium free.

Tertiary phosphines containing 2-thienyl group and their coordination chemistry

Tertiary phosphines containing 2-thienyl group of the type PRnth3-n (R = Me, Et or Ph; th = 2-thienyl; n = 1 or 2) have been prepared and their coordination chemistry has been studied. Series of complexes of the types [PdCl2(PRnth3-n)2]. [PtX2(PRnth3-n)2] (X = Cl, I, Me), [PtXY(PRnth3-n)2] (X = Cl; Y = Me or SnCl3), [PtMe(py)(PRnth3-n)2][PF6], [MCl(μ-Cl)(PR2th)]2 (M = Pd or Pt), [PtCl2(CO)(PR2th)], [RhCl3(PEt2th)3] and [RhCl(CO)(PRnth3-n)2] have been synthesized with these phosphines and characterized by elemental analyses, IR, 1H, 31P, 119Sn, 195Pt NMR spectroscopy. In all the cases phosphine acts as a monodentate ligand with only phosphorus-metal coordination.

Electrosynthesis of triorganylphosphines from organic halides and chlorophosphines, catalyzed by nickel complexes

The possibility of cross coupling of organic halides and chlorophosphines under the action of electrochemically generated Ni(0) complexes of 2,2′-bipy is shown. The final triorganylphosphines are formed by several pathways, including reaction of the σ complex of ArNiX with chlorophosphine and electron transfer-induced reductive elimination of Ph2PArNiX, leading to the cross-coupling product.