7145-06-4

Upstream product

• 762-04-9 Diethyl phosphonate 
• 587-03-1 3-methylbenzyl alcohol 
• 762-04-9 phosphonic acid diethyl ester 
• 620-23-5 m-tolyl aldehyde 
• 814-49-3 diethyl chlorophosphate 

Downstream Products

• 4662-96-8 1,2-di-m-tolylethane 
• 64988-09-6 α-ethoxy-m-xylene 
• 40677-59-6 3-methylbenzyl tert-butyl ether 
• 620-47-3 1-methyl-3-(phenylmethyl)-benzene 
• 21895-16-9 1-methyl-3-(4-methylbenzyl)benzene 
• 38802-08-3 (S)-(-)-tert-butylmethylphenylphosphine oxide 
• 128014-10-8 (R)-(+)-t-butyl(phenyl)phosphinic bromide 
• 6057-79-0 (S)-(-)-t-butyl(phenyl)phosphine oxide 
• 61819-81-6 1,4-dimethyl-2-(3-methylbenzyl) benzene 
• 21895-13-6 1-methyl-2-<(3-methylphenyl)methyl>benzene 
• 35509-94-5 1-(iodomethyl)-3-methylbenzene 

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.

BuLi-triggered phospha-Brook rearrangement: Efficient synthesis of organophosphates from ketones and aldehydes

A variety of organophosphates are synthesized from n-BuLi-triggered, (additional) solvent-free reactions of diethyl phosphite with both activated/unactivated ketones and aldehydes preferably at room temperature via phospha-Brook rearrangement. We could successfully synthesize the naphthylic/allylic phosphates using this approach.

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.

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.