Category: 4141-48-4

Ergueden, Jens Kerim published the artcilePhosphoryl functionalized bishomoallyl alcohols by ring opening of epoxides with lithiated allyldiphenylphosphine oxide, Category: catalysis-chemistry, the publication is Synthesis (1996), 707-710, database is CAplus.

Epoxides are attacked by the lithiated anion of allyldiphenylphosphane oxide in 1,2-dimethoxyethane as solvent in a BF₃.OEt₂ promoted ring opening reaction to afford a mixture of regioisomeric bishomoallyl alcs. (¦Á- and ¦Ã-attack of the nucleophile) in good overall yields. When toluene is used as reaction medium a pronounced preference for ¦Ã-attack of the anion is observed Thus, BF₃.OEt₂ promoted reaction of CH₂:CHCH:P(OLi)Ph₂ with ethyloxirane in DMF gave Ph₂P(O)CH(CH:CH₂)CH₂CHMeOH (diastereomeric mixture) along with Ph₂P(O)CH:CHCH₂CH₂CHMeOH, whereas similar reaction with (tosyloxyethyl)oxirane in PhMe gave Ph₂P(O)CH:CHCH₂CH₂CH(CH₂CH₂OTs)OH.

Synthesis published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Zhang, Zhi-Qi published the artcileDifluoromethylation of Unactivated Alkenes Using Freon-22 through Tertiary Amine-Borane-Triggered Halogen Atom Transfer, Category: catalysis-chemistry, the publication is Journal of the American Chemical Society (2022), 144(31), 14288-14296, database is CAplus and MEDLINE.

The application of abundant and inexpensive fluorine feedstock sources to synthesize fluorinated compounds is an appealing yet underexplored strategy. Here, authors report a photocatalytic radical hydrodifluoromethylation of unactivated alkenes with an inexpensive industrial chem., chlorodifluoromethane (ClCF₂H, Freon-22). This protocol is realized by merging tertiary amine-ligated boryl radical-induced halogen atom transfer (XAT) with organophotoredox catalysis under blue light irradiation A broad scope of readily accessible alkenes featuring a variety of functional groups and drug and natural product moieties could be selectively difluoromethylated with good efficiency in a metal-free manner. Combined exptl. and computational studies suggest that the key XAT process of ClCF₂H is both thermodynamically and kinetically favored over the hydrogen atom transfer pathway owing to the formation of a strong boron-chlorine (B-Cl) bond and the low-lying antibonding orbital of the carbon-chlorine (C-Cl) bond.

Journal of the American Chemical Society published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H21BO3, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Tu, Jianzhuo published the artcileIntramolecular (4+3) Cycloadditions of Oxidopyridinium Ions: Towards Daphnicyclidin A, Recommanded Product: Allyldiphenylphosphine oxide, the publication is Chemistry – A European Journal (2022), 28(41), e202200370, database is CAplus and MEDLINE.

N-alkylation of 5-hydroxynicotinic acid esters with electrophiles containing diene functionality produces salts that underwent intramol. (4+3) cycloaddition reactions upon heating in the presence of base. Initial studies used a three-carbon tether to join the pyridinium ion and diene, revealing some aspects of the inherent selectivity of the reaction with such substrates. Much more challenging was the synthesis of related species possessing only a two-carbon tether. Nevertheless, the cycloaddition of such compounds was successful, leading directly to the ABC ring system of the alkaloid daphnicyclidin A.

Chemistry – A European Journal published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H19BO2, Recommanded Product: Allyldiphenylphosphine oxide.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Lin, Qing-Yu published the artcilePhotoredox-Catalyzed Bromodifluoromethylation of Alkenes with (Difluoromethyl)triphenylphosphonium Bromide, Formula: C15H15OP, the publication is Organic Letters (2016), 18(10), 2419-2422, database is CAplus and MEDLINE.

Under visible-light photoredox conditions, difluoromethyltriphenylphosphonium bromide was used as the precursor of the CF₂H radical for bromodifluoromethylation of alkenes. The presence of catalytic CuBr₂ resulted in the selective formation of the bromodifluoromethylated products. Also, the alkenes underwent bromodifluoromethylation followed by dehydrobromination to give the difluoromethylated alkenes in good yields.

Organic Letters published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Formula: C15H15OP.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Ouvry, Gilles published the artcileSubstituted allyl diphenylphosphine oxides as radical allylating agents, Synthetic Route of 4141-48-4, the publication is Angewandte Chemie, International Edition (2006), 45(30), 5002-5006, database is CAplus and MEDLINE.

The radical addition of dithiocarbonates to branched allyl diphenylphosphine oxides may be followed by elimination of a diphenylphosphinoyl radical, thereby giving rise to allylated products. Highly functionalized structures can thus be rapidly assembled under mild conditions and from cheap and readily available substrates and reagents.

Angewandte Chemie, International Edition published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Synthetic Route of 4141-48-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Chevalley, Alice published the artcileModel Studies for a Ring-Closing Metathesis Approach to the Bafilomycin Macrolactone Core from a 2,2-Dimethoxy Tetraenic Ester Precursor, Name: Allyldiphenylphosphine oxide, the publication is European Journal of Organic Chemistry (2013), 2013(36), 8265-8278, database is CAplus.

A ring-closing metathesis strategy is reported for the construction of the 16-membered macrolactone core of bafilomycin. One decisive key feature is the presence of a 2,2-dimethoxy-ketal functionality at C-2 that provides the required flexibility to the tetraene acid ester precursor, allowing the ring-closing metathesis reaction to take place. Three different model esters of increasing complexity were successfully subjected to the 1,3-diene-ene ring-closing metathesis reaction. The best promoter for the simplest esters was the Grubbs first-generation pre-catalyst. A Hoveyda-Grubbs-type trifluoroacetamide-containing pre-catalyst developed by Mauduit’s group gave satisfactory results for the most complex ester. In all experiments, the (12Z)-configured isomer was obtained as the major product. Subsequent microwave-promoted methanol elimination was achieved on the simplest model compound using camphorsulfonic acid (CSA) as a catalyst. Under these conditions, a (E/Z)-isomerization of the double bond at C-4, as well as ca. 50% isomerization of the (12Z)-double bond into the corresponding (12E)-isomer, were observed The synthesis of the target compounds was achieved using (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylic acid 4,5-di-Me ester as a chiral source. The title compounds thus formed included a maacrolactone (macrolide) (I) and related substances.

European Journal of Organic Chemistry published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Name: Allyldiphenylphosphine oxide.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Rolland, Herve published the artcileUse of tin derivatives for selective allylation and methylation of halophosphorus compounds, Application of Allyldiphenylphosphine oxide, the publication is Tetrahedron Letters (1992), 33(52), 8095-8, database is CAplus.

Palladium(0) catalyzed gem-dimethylation of hexachlorocyclotriphosphazene with tetramethylstannane is described as well as the high yield monoallylation of halophosphorus or -boron compounds by allyltrialkylstannanes under photolytic conditions.

Tetrahedron Letters published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Application of Allyldiphenylphosphine oxide.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Hornillos, Valentin published the artcileCu-Catalyzed Asymmetric Allylic Alkylation of Phosphonates and Phosphine Oxides with Grignard Reagents, Computed Properties of 4141-48-4, the publication is Chemistry – A European Journal (2013), 19(17), 5432-5441, database is CAplus and MEDLINE.

An efficient and highly enantioselective Cu-catalyzed allylic alkylation of phosphonates and phosphine oxides with Grignard reagents and Taniaphos or phosphoramidites as chiral ligands is reported. Transformation of these products leads to a variety of new P-containing chiral intermediates.

Chemistry – A European Journal published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Computed Properties of 4141-48-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Tejo, Ciputra published the artcileDearylation of arylphosphine oxides using a sodium hydride-iodide composite, COA of Formula: C15H15OP, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(14), 1782-1785, database is CAplus and MEDLINE.

A new protocol for the dearylation of arylphosphine oxides was developed using sodium hydride (NaH) in the presence of lithium iodide (LiI). Reaction of triarylphosphine oxides Ar₂PPh with NaH/LiI afforded sodium phosphinites Ar₂PONa, which were trapped with alkyl halides RX to give diarylalkylphosphine oxides Ar₂P(O)R in good to excellent yields. The transient sodium phosphinite could be functionalized with a range of electrophiles in a one-pot fashion.

Chemical Communications (Cambridge, United Kingdom) published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C17H19N3O6, COA of Formula: C15H15OP.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Dabkowski, Wojciech published the artcileStudies on the efficient generation of phosphorus-carbon bonds via a rearrangement of P^III esters catalysed by trimethylhalosilanes, Application of Allyldiphenylphosphine oxide, the publication is Chemistry – A European Journal (2009), 15(7), 1747-1756, database is CAplus and MEDLINE.

Halotrimethylsilanes Me₃SiX (X = Br, I) catalyze rearrangements of tricoordinate phosphorus esters R’R”P-OR into the corresponding phosphoryl systems R’R”P(O)R. This provides a simple and efficient route to a variety of structures containing phosphorus-carbon bonds, under mild conditions and with good yields. The reaction mechanism was investigated in detail by ³¹P NMR spectroscopy and independent synthesis of the reaction intermediates. It has been demonstrated that the primary products of this catalytic reaction are halogeno P^III structures R’R”PX and silyl ethers ROSiMe₃ and that they subsequently react to give the corresponding phosphorus silyl esters -Me₃SiOPR’R”- and alkyl halides RX. At higher temperatures these intermediates then react to form R’R”P(O)R compounds This paper also features the surprising observation that when esters Ph₂POR and halotrimethylsilanes Me₃SiX (X = Br, I) are used in 2:1 ratio, phosphonium salts Ph₂R₂P⁺X^– and trimethylsilyl diphenylphosphinate -Ph₂P(O)OSiMe₃ are formed as the major products. Exptl. evidence indicates that the mechanisms of both reactions are fundamentally different from that of the Michaelis-Arbuzov reaction. Me₃SiCl is not reactive and this paper explains why.

Chemistry – A European Journal published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Application of Allyldiphenylphosphine oxide.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia