2959-60-6

Upstream product

• 1777-57-7 p-bromobenzoylmethylenetriphenylphosphorane 
• 98-80-6 phenylboronic acid 
• 603-35-0 triphenylphosphine 
• 135-73-9 2-Bromo-4'-phenylacetophenone 
• 28160-67-0 (2-oxo-2-p-biphenylethyl)triphenylphosphonium bromide 
• 2928-58-7 (2-oxo-2-p-bromophenylethyl)triphenylphosphonium bromide 

Downstream Products

• 672285-11-9 (E,E)-1,7-bis(4-phenylbenzoyl)-1,6-heptadiene 
• 42169-05-1 1-Biphenyl-4-yl-2-chloro-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 
• 1280739-15-2 (4aS,5R,6S,10bS)-2-(biphenyl-4-yl)-6-(2-(biphenyl-4-yl)-2-oxoethyl)-5-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one 
• 1280739-02-7 (2E,2'E)-3,3'-(1,2-phenylene)bis(1-(biphenyl-4-yl)prop-2-en-1-one) 
• 1542158-94-0 2-(2-([1,1'-biphenyl]-4-carbonyl)-3-(nitromethyl)-2,3-dihydro-1H-inden-1-yl)-1-([1,1'-biphenyl]-4-yl)ethan-1-one 
• 1542159-09-0 C₃₆H₂₆O₂ 

Relevant academic research and scientific papers

Synthesis, spectroscopic and structural characterization of orthopalladated complexes with 4-phenylbenzoylmethylene triphenyl phosphorane ylide

The orthometalated complex [Pd(μ-Cl)(C6H5-C 6H4C(O)CHPPh2C6H4- κ2-C,C)]2 (1) was prepared by refluxing in MeOH/CH2Cl2 equimolecular amounts of Pd(OAc)2 and (Ph)3PCHCOC6H4-Ph-4 (=PhBPPY) followed by addition of excess NaCl. Complex 1 reacts with 4-picoline to give the mononuclear derivative [Pd(PhC6H4- COCHPPh 2C6H4)(4-picoline)] (2) whose crystal structure has been determined by X-ray diffraction. The precursor complex (1) could not be isolated in a pure form, but it can be used as a starting material for the synthesis of derivatives of mononuclear cyclo-palladated complexes. Orthometallation and ylide C-coordination in complexes 3-5 were characterized by elemental analysis as well as various spectroscopic techniques. Springer Science+Business Media B.V. 2010.

Synthesis and multinuclear NMR study of Hg(II), Cd(II), and Pd(II) complexes with biphenylmethylenetriphenylphosphorane: X-ray crystal structure of [{C6H5C6H4CO{(C6H5)3P}CH}HgI2]2

Reactions of title ylide, {(C6H5)3PCHCOC6H4C6H5)} (BPPPY), with mercury(II) halides in equimolar ratios in methanol yielded dinuclear complexes [(BPPPY)HgCl2]2 (1), [(BPPPY)HgBr2]2 (2), and [(BPPPY)HgI2]2 (3). Reactions of BPPPY with CdCl2 in equimolar ratios gave [(BPPPY)CdCl2]2 (4). Reaction of PdCl2 with BPPPY (1/2) in acetonitrile at room temperature gave cis/trans [PdCl2{CH(PPh3)COC6H4C6H5}2] (5). The same reaction at reflux gave the orthopalladated complex [Pd{CH{P(2-C6H4)Ph}(COC6H4C6H5)}(μ-Cl)]2 (6) along with the phosphonium salt [Ph3PCHCOC6H4C6H5]Br. The compounds were characterized by elemental analysis, IR-, 1H-, 13C-, and 31P-NMR spectroscopy. Single crystal X-ray analysis of 3 reveals the centrosymmetric dimeric structure containing the ylide and HgI2. Crystallographic data for 3 are: crystal system, monoclinic; space group, P 21/n, a = 15.7744(7), b = 23.0288(9), c = 20.2867(9)A, β = 112.237(3)°, V = 6821.4(5)A3, and Z = 1.

Silica gel-promoted synthesis of multisubstituted spiroindolenines from tryptamines and γ-chloro-α,β-unsaturated ketones

Here we report a one-pot synthesis of multisubstituted spiroindolenines from a series of tryptamine derivatives with γ-chloro-α,β-unsaturated ketones. The reaction sequence consists of base-induced condensation and silica gel-promoted intramolecular Michael addition. The target molecules are afforded in up to 90% yield with up to >20:1 diastereoselectivity.

Substituent effects in the formation of a few acenaphthenone-2-ylidene ketones and their molecular docking studies and in silico ADME profile

We observed intriguing substituent effects in the reaction between 4-substituted acetophenones and acenaphthenequinone in the presence of KOH in methanol. In all cases, expected Claisen-Schimdt condensation was the first step. However, depending on the nature of 4-substituent on acetophenone, the initially formed condensation product remain unchanged or underwent Domino sequence of reactions to give three different 2:2 adducts arising through three distinct pathways. The interactions of acenaphthenone-2-ylidene ketones with the target proteins were performed by molecular docking studies. The prediction of in silico ADME belongings of the synthesized compounds revealed substantial drug-likeness characters based on Lipinski's rules.

Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor

A convergent strategy is reported for the construction of nitrogen-containing heterocycles from common substrates: 1,4-diketones and primary amines. Indeed, by just varying the substrates, the substituents, or the heating mode, it is possible to selectively synthesize indole, indolone (1,5,6,7-tetrahydroindol-4-one), or cinnoline (5,6,7,8-tetrahydrocinnoline) derivatives in moderate to excellent yields.

Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines

The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.

Rh-Catalyzed diastereoselective desymmetrization of enone tethered-cyclohexadienones: Via tandem arylative cyclization

The rhodium-catalyzed arylative cyclization of enone tethered-cyclohexadienones has been developed with high efficiency, thus providing cis-fused bicyclic enones in good yields and with excellent diastereoselectivities. Furthermore, this mild transformation has a broad range of substrate scope and excellent functional group tolerance. In addition, bicyclic products have an enone functionality, which can be a synthetically valuable handle for further transformations.

Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond to Form Two Stereogenic Centers in an Aqueous Medium

Organocatalytic selenosulfonylation of the C-C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.

A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions

A Ba/Pd cooperative catalysis system was developed to enable the dehydrative cross-coupling of allylic alcohols with P-ylides to occur directly and promote a subsequent Wittig reaction in one pot. A variety of multisubstituted 1,4-dienes were isolated in good to excellent yields with broad P-ylides (stabilized by both ester and ketone carbonyl groups) and aldehyde (aliphatic and aromatic) substrates with excellent E selectivity.

Tandem Wittig Reaction-Ring Contraction of Cyclobutanes: A Route to Functionalized Cyclopropanecarbaldehydes

An original tandem reaction consisting of a Wittig reaction-ring contraction process between α-hydroxycyclobutanone and phosphonium ylides has been developed. Highly functionalized cyclopropanecarbaldehydes are obtained in good to high yield.