76583-99-8

Upstream product

• 2687-12-9 cinnamyl chloride 
• 75-65-0 tert-butyl alcohol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 673-32-5 1-Phenylprop-1-yne 
• 140-10-3 (E)-3-phenylacrylic acid 
• 103-26-4 Methyl cinnamate 
• 16212-06-9 phenyl styryl sulfone 
• 1634-04-4 tert-butyl methyl ether 
• 2327-99-3 1-phenylpropadiene 
• 1907-33-1 lithium tert-butoxide 
• 95932-32-4 tert-butyl (E)-cinnamyl carbonate 

Downstream Products

• 1078-70-2 3-phenylprop-2-enyloxycarbonylamine 
• 76613-60-0 trans-3-phenyl-1-propenyl tert-butyl ether 
• 76584-00-4 cis-3-phenyl-1-propenyl tert-butyl ether 

Relevant academic research and scientific papers

Radical C(sp3)-H alkenylation, alkynylation and allylation of ethers and amides enabled by photocatalysis

An efficient radical addition/elimination reaction that enables selective incorporation of alkenyl, alkynyl and allyl functional groups into the C(sp3)-H bond under green reaction conditions is developed. The process is based on the catalytic formation of α-alkoxyl/α-amidyl radicals via the homolytic activation of the C(sp3)-H bond of ethers/amides with a catalytic amount of diarylketone in the presence of a household fluorescent light bulb. This simple reaction protocol features good functional group tolerance, scalability, convenient reagents and operating systems. Synthetic application of the method has been demonstrated via the preparation of natural products and different valuable synthones.

Multimetallic Ir-Sn3-catalyzed substitution reaction of π-activated alcohols with carbon and heteroatom nucleophiles

An atom economic and catalytic substitution reaction of π-activated alcohols by a multimetallic IreSn3 complex has been demonstrated. The multimetallic IreSn3 complex can be easily synthesized from the reaction between [Cp*IrCl2]2 and SnCl2. In presence of as little as 1 mol % of the catalyst three different types of π-activated alcohols, namely benzyl, allyl, and propargyl alcohols, have been successfully transformed into alkylated products using carbon (arenes, heteroarenes, allyltrimethylsilane, and 1,3-dicarbonyls), nitrogen (sulfonamides), oxygen (alcohols), and sulfur (thiols) nucleophiles in very high yields. An electrophilic mechanism is proposed from the Hammett correlation study.

Regio- and stereoselective Au(I)-catalyzed intermolecular hydroalkoxylation of aryl allenes

In the presence of a catalytic amount of Ph3PAuNO3 and H2SO4, the hydroalkoxylation of allenes with alcohols has been shown to proceed smoothly and give allylic ethers in good yields and high regio- and stereoselectivity. Georg Thieme Verlag Stuttgart.

Iridium-catalyzed intermolecular allylic etherification with aliphatic alkoxides: Asymmetric synthesis of dihydropyrans and dihydrofurans

Hindered chiral ethers with one or two stereocenters are now readily available by allylic etherification of primary and secondary alkoxides (see reaction). When an Ir-phosphoramidite complex is used as the catalyst, the reaction proceeds with high regio-, enantio-, and diastereoselectivity. Np = 1-naphthyl.

Palladium-catalyzed coupling of alkynes with alcohols and carboxylic acids

The palladium-catalyzed coupling of alkynes with alcohols and carboxylic acids to give allylic ethers and esters has been achieved. With phenols, these conditions furnish the C-alkylation products.

Zeolite-HY: A selective and efficient catalyst for the alcoholyses of various alcohols

An efficient and selective method for the conversion of various alcohols into their corresponding ethers in the presence of zeolite under solvolytic condition is described. The reaction proceeds efficiently at ambient pressure in high yields.

tert-Butoxy and 2-furyl. Two effective substituents at stabilizing carbon-carbon double bonds

Potassium tert-butoxide was used as a catalyst at 25°C to establish equilibrium, approached from both sides, in two reactions of the type trans-PhCH = CHCH2X ? trans-PhCH2CH = CHX. At equilibrium in 80% dimethyl sulfoxide-20% tert-butyl alcohol, 4.3% trans-cinnamyl tert-butyl ether, 28.5% trans-3-phenyl-1-propenyl tert-butyl ether, and 67.2% cis-3-phenyl-1-propenyl tert-butyl ether were present. In tert-butyl alcohol, 22.4% trans-3-(2-furyl)-1-phenyl-1-propene, 72.8% trans-1-(2-furyl)-3-phenyl-1-propene, and 4.86% cis-1-(2-furyl)-3-phenyl-1-propene were present at equilibrium. These plus earlier observations show that the "double bond stabilizing abilityquot; of the tert-butoxy group is greater than that of the methoxy group and that the double bond stabilizing ability of the 2-furyl group is greater than that of the phenyl group. Reasons for these differences are discussed. In both cases steric factors are thought to be important.