187344-92-9

Usage

Chemical Properties

White powder

Uses

suzuki reaction

InChI:InChI=1/C16H19OP/c1-11-5-12(2)8-15(7-11)18(17)16-9-13(3)6-14(4)10-16/h5-10,18H,1-4H3

Upstream product

• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 556-96-7 5-bromo-1,3-xylene 
• 762-04-9 Diethyl phosphonate 
• 106-93-4 ethylene dibromide 
• 74289-57-9 bis-(3,5-dimethylphenyl)chlorophosphine 
• 762-04-9 phosphonic acid diethyl ester 

Downstream Products

• 325773-60-2 2,2'-bis-[bis-(3,5-dimethyl-phenyl)-phosphinoyl]-biphenyl 
• 135139-00-3 (S)-2,2'-bis-1,1'-binaphthyl 
• 1443418-92-5 bis(3,5-dimethylphenyl)(2-(pyridin-2-yl)phenyl)phosphine oxide 
• 1527476-49-8 4-((bis(3,5-dimethylphenyl)phosphoryl)(phenyl)methyl)-3-methyl-1-phenyl-1H-pyrazol-5-ol 

Relevant academic research and scientific papers

Synthesis of novel C2 and C1 symmetric chiraphos derivatives and their application in palladium-catalyzed miyauramichael reaction

A new method for the synthesis of C2 and C1 symmetric CHIRAPHOS derivatives and their application in Pd-catalyzed 1,4-addition reaction of an aryl boron compound to an ,￠-unsaturated carbonyl compound (MiyauraMichael reaction) are described. Six CHIRAPHOS congeners are prepared by substitution reactions of (2R,3R)-butane-2,3-diyl ditosylate with metalated phosphineborane adducts and subsequent deprotection of the resulting borane-protected bisphosphines. In the asymmetric MiyauraMichael reaction, the CHIRAPHOS derivative containing 4-tolyl groups showed a higher enantioselectivity than the others including parent CHIRAPHOS.

Electrochemical Oxidative C–H Phosphonylation of thiazole derivatives in ambient conditions

We herein report a direct electrochemical dehydrogenative C–H phosphonylation of thiazoles derivatives with H2 evolution. Employing electricity as the green and sole oxidant, cheap metal as electrode, the anodic oxidation together with cathodic hydrogen evolution process provides a green and efficient strategy for C–H phosphonylation. A diverse range of phosphorus products were constructed under external metal and oxidant-free conditions at ambient temperature, featuring atom economy, simple operation and wide reaction scope.

Highly Enantioselective Synthesis of Phosphorus-Containing ?-Benzosultams by Bifunctional Phosphonium Salt-Promoted Hydrophosphonylation

?-Benzosultam derivatives are potential drug candidates with diverse biological activities. A series of chiral ?-benzosultams bearing phosphorus functionalities was synthesized by catalytic asymmetric hydrophosphonylation in the presence of a bifunctional phosphonium salt catalyst. The desired hydrophosphonylation products were obtained in good yields with high enantioselectivities, and scale-up reactions and further derivations were successfully accomplished. Some control experiments were also conducted to elucidate the plausible reaction mechanism of this chemical transformation.

Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones

A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.

Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles

A metal-free C(sp3)-H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Br?nsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was used for the first time as a photocatalyst and exhibited an excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible light photoredox catalytic oxidation/nucleophilic addition process.

Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids

Hydrogenation of carboxylic acids (CAs) to alcohols represents one of the most ideal reduction methods for utilizing abundant CAs as alternative carbon and energy sources. However, systematic studies on the effects of metal-to-ligand relationships on the catalytic activity of metal complex catalysts are scarce. We previously demonstrated a rational methodology for CA hydrogenation, in which CA-derived cationic metal carboxylate [(PP)M(OCOR)]+ (M = Ru and Re; P = one P coordination) served as the catalyst prototype for CA self-induced CA hydrogenation. Herein, we report systematic trial- and-error studies on how we could achieve higher catalytic activity by modifying the structure of bidentate diphosphine (PP) ligands of molecular Ru catalysts. Carbon chains connecting two P atoms as well as Ar groups substituted on the P atoms of PP ligands were intensively varied, and the induction of active Ru catalysts from precatalyst Ru(acac)3 was surveyed extensively. As a result, the activity and durability of the (PP)Ru catalyst substantially increased compared to those of other molecular Ru catalyst systems, including our original Ru catalysts. The results validate our approach for improving the catalyst performance, which would benefit further advancement of CA self-induced CA hydrogenation.

Cinchona alkali ligand and preparation method and application thereof

The invention belongs to the field of organic chemical ligands, and particularly relates to a cinchona alkali ligand, which has a structure shown in a general formula I or a tautomer, an enantiomer and a diastereoisomer thereof, in the formula I, R1 is selected from alkyl, alkenyl and -CH = CHPh, R2 is selected from hydrogen, alkyl, phenyl and substituted phenyl, and R is selected from substituted phenyl. The invention also discloses a preparation method and application of the cinchona alkaloid ligand. The ligand disclosed by the invention has advantages in stereoselectivity and reaction efficiency, and a higher ee value and yield can be obtained in an asymmetric reaction.

Enantioselective hydrophosphinylation of 1-alkenylphosphine oxides catalyzed by chiral strong Br?nsted base

A catalytic enantioselective addition of diarylphosphine oxides to 1-alkenyl(diaryl)phosphine oxides was achieved by using a chiral ureate as a chiral strong Br?nsted base catalyst. The reaction followed by the reduction of phosphine oxide moieties provid

Transition Metal-Free Synthesis of α-Aminophosphine Oxides through C(sp3)?P Coupling of 2-Azaallyls

Radical reactions have been widely applied in C?P bond-forming strategies. Most of these strategies require initiators, transition metal catalysts, or organometallic reagents. Herein, a transition metal-free C(sp3)?P bond formation to prepare α

An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides

An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method.