88539-06-4

Upstream product

• 66482-29-9 1-[(E)-2-bromoethenyl]-4-chlorobenzene 
• 1073-67-2 4-vinylbenzyl chloride 
• 52147-98-5 2(E)-(4-chlorophenyl)ethenesulfonyl chloride 
• 109391-62-0 C₁₆H₁₂Cl₂ 
• 154230-29-2 (E)-4-chlorostyrylboronic acid 

Relevant academic research and scientific papers

Pd-catalyzed oxidative homo-coupling of acrylates and aromatic alkenes for the conjugated diene synthesis

We developed a bidentate monoanionic nitrogen ligand that was effective in the Pd-catalyzed oxidative homo-coupling reaction of acrylates and aromatic alkenes. In the presence of Pd(OAc)2/ligand several conjugated dienes were obtained in good yields with high stereoselectivities.

Synthesis of Buta-1,3-dienes through Palladium-Catalyzed Homocoupling of Aromatic Alkenes

A series of buta-1,3-dienes have been directly synthesized via a convenient palladium-catalyzed homodehydrogenation coupling reaction of aromatic alkenes under mild conditions. The homocoupling reaction enables a rapid synthesis of multisubstituted butadiene which shows typical aggregation-induced emission enhancement (AIEE) characteristics because it is practically not emissive in solution but emits blue fluorescence in aggregates.

Homocoupling of arylboronic acids with a catalyst system consisting of a palladium(II) N-heterocyclic carbene complex and p-benzoquinone

In the presence of 1-3 mol% SIPr-ligated Pd(OAc)2 and 0.6 equivalent of p-benzoquinone, various arylboronic acids underwent homocoupling in MeOH at ambient temperature to produce symmetrical biaryls in 38-96% yields. Georg Thieme Verlag Stuttgart.

Oxidative dimerization: Pd(II) catalysis in the presence of oxygen using aqueous media

Reported herein is a method for the formation of symmetric biaryls and dienes via oxidative dimerization of aryl and alkenyl boronic acids. These conditions utilized Pd(II) catalysts under an oxygen atmosphere with water as the solvent. The use of phase transfer catalysts promoted efficient and mild syntheses of a wide range of materials.

Ni(0)-Triphenylphosphine Complex-Catalyzed Homo-Coupling of 1-Alkenyl Halides with Zinc Powder

The homo-coupling of 1-alkenyl halides was examined in the presence of NiBr2(PPh3)2, PPh3, and excess zinc.The reactions proceed under very mild conditions to give high yields of conjugated dienes.The addition of KI or thiourea was unnecessary for a successful reaction, in contrast with systems without an external phosphine ligand.

REDUCTIVE DIMERIZATION OF VINYL HALIDES IN AN Ni/Pb/Al THREE METAL REDOX SYSTEM. A FACILE ACCESS TO TERPHENYL DERIVATIVES

A novel three metal redox system, NiCl2(bpy)/PbBr2/Al, is found to be potent in the reductive coupling of vinyl halides, affording 1,4-biaryl-1,3-butadienes, precursors of terphenyl derivatives.

A NOVEL SYNTHESIS OF (E,E)-1,4-DIARYL-1,3-BUTADIENES BY THE RUTHENIUM(II) CATALYZED REACTION OF (E)-2-ARYLETHENESULFONYL CHLORIDES WITH VINYLARENES

Symmetrical and unsymmetrical (E,E)-1,4-diaryl-1,3-butadienes can be prepared in high yields from (E)-2-arylethenesulfonyl chlorides by treating with vinylarenes in the presence of ruthenium(II) phosphine complex in benzene.

Reaction of Alkenesulfonyl Chlorides with Olefins Catalyzed by a Ruthenium(II) Complex. A Novel Method for Synthesis of (E,E)-1,4-Diaryl-1,3-butadienes

In the presence of a catalytic amount of dichlorotris(triphenylphosphine)ruthenium(II) (1), alkenesulfonyl chloride (2) was found to react with vinylarenes to give 1:1 adducts (3) in high yield under mild conditions.Dehydrochlorination from the adducts 3 to afford divinyl sulfones (4) takes place by raising the reaction temperature from 80 to 130 deg C.Upon further reaction at 150 deg C, (E,E)-1,4-diaryl-1,3-butadienes (5) are formed in high yield if both of the alkenyl substituents of the sulfonyl chloride and the alkene have aryl groups.The time course of the reaction indicates that the addition of 2 to vinylarenes giving 1:1 adducts 3, dehydrochlorination from the adducts 3 giving divinyl sulfones 4, and desulfonylation from the divinyl sulfone 4 giving 1,3-butadienes 5 proceed successively.The usefulness of the reaction for the syntheses of (E,E)-1,4-diaryl-1,3-butadiene is described.On the other hand, 2 reacts with alkyl olefins in the presence of 1 to give 1:1 adducts (12) with extrusion of sulfur dioxide.

IN SITU-GENERATED NICKEL(0)-CATALYZED HOMO-COUPLING OF ALKENYL HALIDES WITH ZINC POWDER. A SPECIFIC OUTCOME IN STEREOCHEMISTRY.

The catalytic activity of nickel(0) generated in situ from nickel(II) salt was examined in a dehalogenative coupling of alkenyl halides with zinc powder. The reaction of alkenyl bromides took place provided that potassium iodide was present to assist the reduction of nickel(II) with zinc powder, and also to convert the alkenyl bromides to the corresponding alkenyl iodides. A speculative view concerning the disproportionation step is advanced in an attempt to explain the unique sterochemistry observed.