22440-35-3

Upstream product

• 4714-21-0 4-methylstilbene 
• 1657-45-0 (Z)-4-methylstilbene 
• 128160-29-2 C₁₉H₃₄BrSb 
• 104-87-0 4-methyl-benzaldehyde 
• 134988-30-0 benzyldibutyltelluronium bromide 
• 4714-21-0 E-1-methyl-4-styryl-benzene 
• 100-52-7 benzaldehyde 
• 40154-39-0 p-tolualdehyde tosylhydrazone Na salt 
• 100-39-0 benzyl bromide 
• 104-81-4 4-Methylbenzyl bromide 
• 100-51-6 benzyl alcohol 
• 114552-49-7 (+)-(1R,2S,3R,4S)-1,7,7-Trimethyl-3-(benzylthio)bicyclo<2.2.1>heptan-2-ol 
• 908094-04-2 phenyldiazomethane 
• 27992-27-4 sodium 2-benzylidene-1-tosylhydrazin-1-ide 

Downstream Products

• 50600-30-1 2-(4-methylphenyl)-2-(phenyl)acetaldehyde 
• 134-84-9 4-Methylbenzophenone 
• 22440-35-3 trans-(2R,3R)-2-(4-methylphenyl)-3-phenyl oxirane 
• 20498-63-9 1-(4-methylphenyl)-2-phenylethanol 
• 104-87-0 4-methyl-benzaldehyde 
• 100-52-7 benzaldehyde 
• 100-47-0 benzonitrile 
• 104-85-8 para-methylbenzonitrile 
• 102459-54-1 phenyl-carbamic acid-(4-methyl-bibenzyl-α-yl ester) 
• 890654-72-5 3-(4-methylphenyl)-3-phenylprop-1-ene-1,1-dicarbonitrile 
• 2430-99-1 1-phenyl-2-p-tolylethanone 
• 50600-29-8 phenyl-2-p-tolyl-ethane-1,2-diol 

Relevant academic research and scientific papers

Synthesis of Epoxides from Alkyl Bromides and Alcohols with in Situ Generation of Dimethyl Sulfonium Ylide in DMSO Oxidations

Direct conversion of the readily available alkyl bromides and alcohols to value-added epoxides using dimethyl sulfoxide (DMSO) under mild reaction conditions has been developed. Benzyl and allyl bromides, and activated and unactivated alcohols all proceeded smoothly to give epoxides in high to excellent yield. Dimethyl sulfide, generated by DMSO oxidations, was in situ elaborated to form the substituted dimethyl sulfonium ylide species that participates in the Corey-Chaykovsky epoxidation in a domino and one-pot fashion, respectively.

Method used for direct synthesis of epoxy compounds from alcohol

The invention discloses a method used for direct synthesis of an epoxy compounds from an alcohol. According to the method, an alcohol is taken as a raw material, Swern oxidation is adopted to synthesize an aldehyde, a bromo-hydrocarbon and an alkali are added into the aldehyde directly to construct epoxy functional groups, and generate the epoxy compound. According to the method, one-pot method is adopted to realize direct epoxidation of the alcohol, the synthesis route is simple, the preparation process is easy to control, no catalyst is needed in the process, substrate suitable range is wide, reagents are cheap and easily available, preparation conditions are mild, reaction yield is high, and the method is suitable for synthesis of epoxy compounds.

Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide

Among chiral macrocycles 1 synthesized, 1m with the 3,5-bis(trifluoromethyl)phenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO2. The X-ray crystal structure of 1m revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of epoxides. A catalytic cycle proposed was supported by DFT calculations.

Benzylic Ammonium Ylide Mediated Epoxidations

A high yielding synthesis of stilbene oxides using ammonium ylides has been developed. It turned out that the amine leaving group plays a crucial role as trimethylamine gives higher yields than DABCO or quinuclidine. The amine group also influences the diastereoselectivity, and detailed DFT calculations to understand the key parameters of these reactions have been carried out.

Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Br?nsted-acidic ionic liquids (ILs), and IL/microwave; Experimental and computational substituent effect study on aryl versus hydrogen migration

The Lewis-acid catalyzed rearrangement of parent trans-stilbene oxide 1 was studied with M(OTf)3/DCM and M(OTf)3/[BMIM][BF 4] (M = Bi, Al, Ga, Sc, and Yb; [BMIM] = butylmethylimidazolium) and Zn(NTf2)2, and with Bi(OTf)3/[BMIM][X] (X = NTf2, OTf, PF6, and BF4), employing 5 mol% of catalyst. Selective formation of 2,2-dipheylacetaldehyde 2 (phenyl migration product) was observed in all cases, with Bi(OTf)3 proving most efficient. The rearrangement of 1 was also effected in [BMIM][X] (X = NTf 2, OTf, PF6, and BF4) without an added catalyst under microwave MW irradiation, and X = PF6 gave the highest yield and selectivity. Efficient and selective rearrangement of 1-2 was also observed with 0.1-0.3 equiv. of [BMIM(SO3H)][OTf] in DCM and in [BMIM][X]. A substituent effect study was performed with a series of singly substituted 1,2-diphenyl oxiranes (with X = OMe, Me, F, CN, and NO2) with 5 mol% Bi(OTf)3 in DCM and in [BMIM][NTf2]. Notable formation of ketones was observed with the NO2 and CN derivatives. Competing formation of ketones was also observed in [BMIM][PF6] under MW and under Br?nsted acid catalysis with [BMIM(SO3H)][OTf] in DCM and in [BMIM][NTf2]. The aryl versus H migration was studied computationally by DFT and MP2 methods and by including solvation effects (IEFPCM).

Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Br?nsted-acidic ionic liquids (ILs), and IL/microwave; experimental and computational substituent effect study on aryl versus hydrogen migration

The Lewis-acid catalyzed rearrangement of parent trans-stilbene oxide 1 was studied with M(OTf)3/DCM and M(OTf)3/[BMIM][BF4] (M = Bi, Al, Ga, Sc, and Yb; [BMIM] = butylmethylimidazolium) and Zn(NTf2)2, and with Bi(OTf)3/[BMIM][X] (X = NTf2, OTf, PF6, and BF4), employing 5 mol% of catalyst. Selective formation of 2,2-dipheylacetaldehyde 2 (phenyl migration product) was observed in all cases, with Bi(OTf)3 proving most efficient. The rearrangement of 1 was also effected in [BMIM][X] (X = NTf2, OTf, PF6, and BF4) without an added catalyst under microwave MW irradiation, and X = PF6 gave the highest yield and selectivity. Efficient and selective rearrangement of 1-2 was also observed with 0.1-0.3equiv. of [BMIM(SO3H)][OTf] in DCM and in [BMIM][X]. A substituent effect study was performed with a series of singly substituted 1,2-diphenyl oxiranes (with X = OMe, Me, F, CN, and NO2) with 5mol% Bi(OTf)3 in DCM and in [BMIM][NTf2]. Notable formation of ketones was observed with the NO2 and CN derivatives. Competing formation of ketones was also observed in [BMIM][PF6] under MW and under Br?nsted acid catalysis with [BMIM(SO3H)][OTf] in DCM and in [BMIM][NTf2]. The aryl versus H migration was studied computationally by DFT and MP2 methods and by including solvation effects (IEFPCM).

Enantioselective synthesis of (thiolan-2-yl)diphenylmethanol and its application in asymmetric, catalytic sulfur ylide-mediated epoxidation

This work describes an expeditious and efficient preparation of enantiopure (thiolan-2-yl)diphenylmethanol (2) featuring a double nucleophilic substitution and Shi epoxidation as key steps. One of the applications of its benzyl ether derivative to asymmetric sulfur ylide-mediated epoxidation with up to 92% ee (14 examples) was also demonstrated herein.

Sequential- and tandem-oxidation-epoxidation reactions employing guanidine bases

1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD) and 7-methyl-1,5,7- triazabicyclo[4.4.0]dec-1-ene (MTBD) promote the efficient formation of sulfonium ylides from sulfonium salts in the Corey-Chaykovsky epoxidation of aldehydes and provide excellent yields of the corresponding epoxides. This reaction protocol can be further adapted to allow for the development of both sequential and tandem-oxidation-epoxidation protocols from aldehydes generated in situ by manganese dioxide (MnO2) or barium manganate (BaMnO 4) mediated oxidation reactions.

A non-heme iron(III) complex with porphyrin-like properties that catalyzes asymmetric epoxidation

In this report, we describe an iron(III) complex containing a carbazole-based tridentate ligand that catalyzes highly enantioselective asymmetric epoxidation of (E)-alkenes at room temperature. The non-heme iron(III) complex has a five-coordinated trigonal-bipyramidal structure, and its two-electron oxidized state has the similar electronic structure as that of iron porphyrins.

A new chiral organosulfur catalyst for highly stereoselective synthesis of epoxides

A new chrial organosulfide was synthesized through an unexpected Wagner-Meerwein rearrangement. This organosulfide could catalyze the epoxidation reaction of various aromatic aldehydes smoothly with benzyl bromide to give trans-diaryl epoxides in satisfactory yields (60-84%) with excellent diastereoselectivities (trans:cis=95:5-100:0) and good to excellent enantioselectivities (86-96% ee).