14906-74-2

Upstream product

• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 188290-36-0 thiophene 
• 74785-32-3 (E)-cinnamyl(tributyl)tin 
• 127118-94-9 ethyl(difluoro)(2-thienyl)silane 
• 106625-69-8 ethyl (E)-3-phenyl-2-propenyl carbonate 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 6165-68-0 thiophene boronic acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 7214-53-1 (E)-[2-(phenylsulfanyl)vinyl]benzene 
• 21023-22-3 tri(thiophen-2-yl)indium 
• 2687-12-9 cinnamyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 
• 103-26-4 Methyl cinnamate 

Relevant academic research and scientific papers

CU(I)-Catalyzed regioselective synthesis of substituted allyl furans and thiophenes using organostannanes

2-Allyl-substituted furans and thiophenes were efficiently synthesized from organostannyl derivatives as starting materials using Cu(I) as catalyst. The effect of DMF and NMP as solvents are discussed, as well as other solvent and temperature effects.

Palladium-catalyzed reaction of γ-silylated allyl acetates proceeding through 1,2-shift of a substituent on silicon

The palladium-catalyzed reaction of γ-silylated allyl acetates with water in the presence of CsF induces a previously unprecedented 1,2-shift of a substituent on silicon to produce allylsilanes in situ. The catalytic activity of the palladium increased when using an electron-poor phosphine ligand possessing fluorinated substituents. Further investigation of the reaction revealed that the approximate order of the migratory aptitude of groups from silicon was PhC≡C, allyl > Bn > Ph, vinyl > alkyl (Me, Et). A density functional theory study was employed to explore the reaction mechanism. Finally, the Hosomi–Sakurai-type allylation of aldehydes with in situ-generated α,γ-disubstituted allylsilanes was also investigated.

Synthesis of bench-stable solid triorganoindium reagents and reactivity in palladium-catalyzed cross-coupling reactions

Bench-stable solid triorganoindium compounds have been prepared by coordination with 4-(dimethylamino)pyridine (DMAP). The solid R3In(DMAP) complexes are obtained from the corresponding solution of R3In in quantitative yield and can

Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes or 3-aryl/alkenyl-substituted (E)-(but-1-enyl)benzene. Reaction of allyl alcohol with p-Me2NC6H4ZnCl resulted in a mixture of normal coupling product 4-allyl-N,N-dimethylaniline and its isomerized product N,N-dimethyl-4-(prop-1-en-1-yl)aniline.

Copper-catalysed α-selective allylic alkylation of heteroaryllithium reagents

2-Allyl-substituted thiophenes and furans are synthesised efficiently in a direct procedure using 2-heteroaryllithium reagents and allyl bromides and chlorides catalysed by ligand-free copper(i). The reactions take place under mild conditions, with excellent α-selectivity, high functional group tolerance and good yields for the SN2 products. This journal is

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.

Rhodium-catalyzed allylic substitution reactions with indium(III) organometallics

A novel rhodium-catalyzed allylic substitution reaction using indium organometallics is reported. Aryl- and heteroarylindium reagents reacted in THF at 80 °C with primary and secondary allyl halides and their derivatives under rhodium(I) catalysis to afford the α-substituted products in good yields and with high regio- and stereoselectivity. The reaction takes place with substoichiometric amounts of the triorganoindium reagents, which demonstrates the efficiency of the indium-rhodium transmetallation process in carbon-carbon bond-forming reactions. Copyright

Homogeneous silver(I) salts and heterogeneous Ag3PW 12O40-catalyzed intermolecular allylation of arenes with allylic alcohols

AgOTf is an effective catalyst for intermolecular allylation of aromatic and heteroaromatic compounds with allylic alcohols affording allylated arenes in up to 99% yields. Heterogeneous allylation of arenes catalyzed by Ag 3PW12O40 gave comparable product yields to those obtained by AgOTf. Ag3PW12O40 could be reused five times with slightly decreased activity. Georg Thieme Verlag Stuttgart · New York.

Nickel-catalyzed cross-coupling reaction of allyl- and benzylzinc with alkenyl sulfides

Alkenyl Sulfides can be utilized for nickel-catalyzed cross-coupling reactions with allyl- and benzylzinc reagents.

Rhodium-catalyzed cross-coupling of allyl alcohols with aryl- and vinylboronic acids in ionic liquids

The direct coupling of aryl-and vinylboronic acids with allylic alcohols has been achieved in ionic liquids using a rhodium catalyst.