40156-88-5

Upstream product

• 814-49-3 diethyl chlorophosphate 
• 105-13-5 4-Methoxybenzyl alcohol 
• 123-11-5 4-methoxy-benzaldehyde 
• 762-04-9 phosphonic acid diethyl ester 

Downstream Products

• 1657-55-2 1,2-bis(4-methoxyphenyl)ethane 
• 55249-73-5 1-ethoxymethyl-4-methoxybenzene 
• 56636-80-7 tert-butyl p-methoxybenzyl ether 
• 52126-09-7 4-(4-methoxyphenylmethyl)benzonitrile 
• 1369423-34-6 (S)-4-(4-methoxybenzyl)-4-(2-(methylthio)ethyl)-2-phenyloxazol-5(4H)-one 
• 1369423-29-9 (S)-4-methyl-4-(4-methoxybenzyl)-2-phenyloxazol-5(4H)-one 
• 1369423-39-1 (R)-4-(4-methoxy-3-methylbenzyl)-4-methyl-2-phenyloxazol-5(4H)-one 
• 1369423-35-7 (R)-4-benzyl-4-(4-methoxybenzyl)-2-phenyloxazol-5(4H)-one 
• 1369423-33-5 (R)-4-isobutyl-4-(4-methoxybenzyl)-2-phenyloxazol-5(4H)-one 
• 834-14-0 p-benzylanizole 
• 38802-08-3 (S)-(-)-tert-butylmethylphenylphosphine oxide 
• 128014-10-8 (R)-(+)-t-butyl(phenyl)phosphinic bromide 
• 18648-74-3 2,2-diphenyl-1-(4-methoxyphenyl)ethylene 
• 726-18-1 4,4'-dianisylmethane 

Relevant academic research and scientific papers

Palladium/Xiao-Phos-Catalyzed Kinetic Resolution of sec-Phosphine Oxides by P-Benzylation

P-stereogenic tert- and sec-phosphines have wide applications in asymmetric catalysis, materials, and pharmaceutical chemistry, however, their practical synthesis still constitutes a significant challenge. Herein, a successful kinetic resolution of rac-se

Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)3-Catalyzed Friedel–Crafts-Type Benzylation

Al(OTf)3 was identified as a high-performance catalyst for Friedel–Crafts-type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol-% of the catalyst. A series of diarylmethanes (21 examples) was obtained in moderate to high yield. The catalyst showed unique chemoselectivity, preferentially converting the benzylic phosphate motif, even with a benzylic acetate group existed in the same molecule.

Coupling of arylboronic acids with benzyl halides or mesylates without adding transition metal catalysts

We report herein a transition-metal-free coupling reaction of arylboronic acids with benzyl halides and mesylates for the construction of C(sp2)[sbnd]C(sp3) bonds. A unique feature of this coupling reaction is the formation regioisomers in some cases. Mechanistic studies suggest that this reaction may proceed via an unprecedented Friedel–Crafts-type reaction pathway under base conditions with the assistance of boronic acid moiety.

Synthesis of diarylmethanes through palladium-catalyzed coupling of benzylic phosphates with arylsilanes

An efficient approach to the benzylation of arenes has been developed. The reactions described provide straightforward access to diarylmethanes through Pd-catalyzed coupling of benzylic phosphates with arylsilanes in good to excellent yields. The reaction tolerates a wide range of functionalities such as halide, alkoxyl, and nitro groups.

Synthesis of functionalized diarylmethanes via a copper-catalyzed cross-coupling of arylmagnesium reagents with benzylic phosphates

A combination of copper chloride, triethyl phosphite, and tetrabutylammonium iodide is a very efficient catalytic system for the synthesis of polyfunctionalized diarylmethanes, using the cross-coupling reaction of arylmagnesium halides with benzylic phosphates. The antibiotic Trimethoprim has been prepared using this Cu(I)-catalyzed cross-coupling in 52% overall yield (four steps).

Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids

(Chemical Equation Presented) Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids was investigated. Optimum conditions employed the simple catalytic system of palladium(II) acetate (1 mol %) and triphenylphosphine (4 mol %) with either potassium phosphate or potassium carbonate as the base and toluene as the solvent at 90°C. Using the developed conditions, a series of structurally diverse diarylmethanes were prepared.

Photochemistry of phosphate esters: An efficient method for the generation of electrophiles

The photochemical cleavage of benzyl diethyl phosphates, 1a-g, has been examined in tert-butyl alcohol, which produces the corresponding benzyl tert-butyl ether as the major solvolysis product upon direct irradiation. The multiplicity of the reactive excited state has been established as the singlet state. Evidence favoring an intermediate benzyl cation-phosphate ion pair formed from photofragmentation includes oxygen-18 scrambling, racemization of chiral benzyl phosphates, and substituent effects on the rate of reaction. The existence of an electrophilic intermediate is further supported by a linear free energy relationship for the rate of disappearance of 1, kdis, with Hammett σ, which gave a ρ value of -0.90 and for the rate of appearance of 2, kapp, a Hammett ρ value of -0.97. Possible mechanisms including an electron transfer either before or after homolysis or simple heterolysis of the ester bond are evaluated.