63757-30-2

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 104-88-1 4-chlorobenzaldehyde 
• 2272-55-1 (2R,3S)-ethyl 3-phenylglycidate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 105-36-2 ethyl bromoacetate 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 873-76-7 para-Chlorobenzyl alcohol 
• 65946-56-7 1-ethoxy-1-(trimethylsiloxy)-2-(trimethylsilyl)ethene 
• 6655-32-9 N'-(4-chlorobenzylidene)-2-nitrobenzenesulfonohydrazide 
• 17577-28-5 (ethoxycarbonylmethyl)triphenylphosphonium chloride 
• 104-86-9 4-chlorobenzylamine 
• 637-87-6 1-Chloro-4-iodobenzene 
• 623-47-2 propynoic acid ethyl ester 
• 20026-96-4 ethyl 3-(4-chlorophenyl)propiolate 

Downstream Products

• 80896-74-8 (3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid 
• 1039768-34-7 (S)-3-(4-chlorophenyl)-3-(dimethylphenylsilyl)propanoic acid ethyl ester 
• 5676-62-0 (Z)-3-(4-chlorophenyl)acrylic acid 

Relevant academic research and scientific papers

Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents

We have developed hypervalent iodine(iii) induced oxidative olefination of primary and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.

Atomically precise palladium nanocluster catalyzed tandem oxidation processes of alcohols and phosphorous ylides: Facile access to α,β-unsaturated esters

The mesoporous silica nanosphere supported palladium nanocluster was synthesized through a simple impregnation method and well characterized. The as prepared catalyst shows excellent catalytic performance in tandem oxidation process (TOP) of alcohol and phosphorous ylide, which provides an efficient access to α,β-unsaturated esters with high yields utilizes 1 atmosphere of molecular oxygen as sole oxidant. This work represents the first example of atomically precise palladium nanocluster catalyzed tandem oxidation process of alcohol and phosphorous ylide and is expected to open new horizons for nanoclusters in the tandem reactions.

Gold-catalyzed partial hydrogenation of activated alkynes mediated by triphenylphosphine

Gold(I) can exhibit a cooperative effect with triphenylphosphine, accelerating the triphenylphosphine-mediated partial hydrogenation of activated alkynes. In this protocol, 3-arylpropiolates are selectively reduced to the Z -isomer when the aryl ring bears an electron-donor substituent, whereas 3-arylpropynones are reduced to the E-isomers.

Facile synthesis of α, β-unsaturated esters through a one-pot copper-catalyzed aerobic oxidation-Wittig reaction

An efficient one-pot synthesis of α, β-unsaturated esters through the aerobic oxidation – Wittig tandem reaction of alcohols and phosphorous ylide is developed. This new method operates under mild reaction conditions, and uses CuI/TEMPO (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) as co-catalyst and air (O2) as the oxidant. It tolerates a wide range of functionalized benzylic alcohol and aliphatic alcohols.

One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts

A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.

Phosphine-mediated partial reduction of alkynes to form both (E)- and (Z)-alkenes

A mild, phosphine-mediated partial reduction of alkynyl carbonyls to the corresponding alkenes was developed. Tuning of the reaction conditions led to either the (E)- or (Z)-diastereomer with high selectivity. A range of alkynyl esters, amides, and ketones were reduced to form alkenes in good to high yields and with excellent functional group tolerance.

Silver-Catalyzed Cross-Olefination of Donor and Acceptor Diazo Compounds: Use of N-Nosylhydrazones as Diazo Surrogate

The cross-olefination reaction of donor and acceptor diazo compounds was explored. The use of N-nosylhydrazones as diazo surrogates and the dependence on silver catalysis were crucial for the reaction development. A variety of (hetero)aryl N-nosylhydrazones and α-diazo esters, amides, and phosphonates were compatible, and the functionalized alkene products were afforded in good to high yields with moderate (Z)/(E) selectivities. The experimental and DFT calculation results suggest that the cross-selectivity is due to selective activation of the silver catalyst for donor diazo compounds.

BF3·OEt2-mediated: Syn -selective Meyer-Schuster rearrangement of phenoxy propargyl alcohols for Z -β-aryl-α,β-unsaturated esters

Synthesis of Z-β-aryl-α,β-unsaturated esters from readily available 1-aryl-3-phenoxy propargyl alcohols is achieved via a BF3-mediated syn-selective Meyer-Schuster rearrangement under ambient conditions. The reaction mechanism is postulated to involve an electrophilic borylation of an allene intermediate as the key step to kinetically control the stereoselectivity.

N-heterocyclic carbene-catalysed Peterson olefination reaction

N-heterocyclic carbenes (NHCs) have been utilised as highly efficient organocatalysts to catalyse Peterson olefination reaction of aldehydes with trimethylsilylketene ethyl trimethylsilyl acetal or fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal to produce the corresponding functionalized olefines in 34-93% yields with excellent stereoselectivities.

Iron(IV)-Corrole Catalyzed Stereoselective Olefination of Aldehydes with Ethyl Diazoacetate

Iron(IV)-corrole complexes were first investigated as catalysts for olefination of aldehydes with ethyl diazoacetate in the presence of triphenylphosphine. Efficient olefination of aromatic aldehydes with high trans-selectivity was observed, showing iron corrole is a new kind of promising catalyst for olefination reaction. Transformation of the phosphazine to ylide by iron(IV) corrole was proved to be the key step in the present system.