68826-53-9

Upstream product

• 49639-03-4 (cyclohex-1-enyl)methyl phenyl sulfone 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 930-66-5 1-chlorocyclohexene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 89984-53-2 1-Cyclohexenylmethyldiethoxysilane 
• 7422-28-8 (E)-2-phenylethenyl(trimethyl)stannane 
• 140653-98-1 1-Phenyl-spiro[2.5]octan-4-ol 
• 36839-95-9 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonic acid cyclohex-1-enyl ester 
• 253797-51-2 1-[(2-hydroxy-2-phenyl-1-phenylsulfanyl)ethyl]cyclohexanol 
• 3561-67-9 bis(phenylthio)methane 
• 108-94-1 cyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 

Downstream Products

• 854220-13-6 2-cyclohex-1-enyl-3-phenyl-oxirane 
• 1383536-99-9 4-phenyl-3a,4,7,8,9,9a-hexahydronaphtho[1,2-c]furan-1,3(6H,9bH)-dione 
• 1383537-00-5 2,4-diphenyl-3a,4,6,7,8,9,9a,9b-octahydro-1H-benzo[e]isoindole-1,3(2H)-dione 
• 1396021-79-6 (R,E)-N-[N-(S)-(p-toluenesulfonyl)-p-toluenesulfonimidoyl]-3-styrylcyclohex-2-enamine 

Relevant academic research and scientific papers

Catalytic Chemoselective and Stereoselective Semihydrogenation of Alkynes to E-Alkenes Using the Combination of Pd Catalyst and ZnI2

An efficient E-selective semihydrogenation of internal alkynes was developed under low dihydrogen pressure and low reaction temperature from commercially available reagents: Cl2Pd(PPh3)2, Zn0, and ZnI2. Kinetic studies and control experiments underline the significant role of ZnI2 in this process under H2 atmosphere, establishing that the transformation involves syn-hydrogenation followed by isomerization. This simple and easy-to-handle system provides a route to E-alkenes under mild conditions.

Enabling the Rearrangement of Unactivated Allenes to 1,3-Dienes by Use of a Palladium (0)/Boric Acid System

A redox neutral rearrangement of an allene to a 1,3-diene by means of a unique palladium hydride complex is reported. The palladium hydride complex is generated from a simple Pd 0 source and boric acid [B(OH) 3 ], which is typically identified as a waste by-product of the Suzuki-Miyaura reaction. A mechanism for this transformation using this novel palladium hydride complex is presented; using a direct sample loop and flow injection ESI-HRMS analysis we have detected and identified key π-allylpalladium complexes that support the addition of the palladium hydride complex to the allene.

Synthesis of 1,3-Dienes via a Sequential Suzuki-Miyaura Coupling/Palladium-Mediated Allene Isomerization Sequence

We report a facile method for the synthesis of 1,3-dienes by a sequential process consisting of a palladium-catalyzed, base-free, Suzuki-Miyaura coupling/isomerization sequence. This sequence couples boronic acids with propargyl alcohols, generating the requisite allene in situ, followed by conversion of the unactivated allene to its 1,3-diene via a hydro-palladation/dehydro-palladation process. This process is general for a range of boronic acids, including boronic acids with electron-donating and -withdrawing groups, as well as heteroarylboronic acids. Key to this process is the boric acid byproduct of the base-free Suzuki-Miyauru coupling, which generates the required palladium-hydrido complex [H-PdII-OB(OH)2] required for the isomerization.

Stereoselective synthesis of 1,3-dienes from propargylic alcohols by LiAlH4/AlCl3

Herein we report that LiAlH4/AlCl3 is a very efficient reagent for the reductive dehydration of aryl propargylic alcohols in tetrahydrofuran solvent at reflux to give 1,3-dienes with good yields and high E selection. The reaction con

Ligand effects on the stereochemical outcome of suzuki-miyaura couplings

The ligands associated with various Pd catalysts play a crucial role in determining the stereochemistry of cross-couplings between boronic acids and Z-alkenyl halides. A ligand on palladium has been found that leads to the desired products under mild conditions and in high yields that, in most cases, retain their Z-olefin geometry.

Gold-catalyzed isomerization of unactivated allenes into 1,3-dienes under ambient conditions

We have developed a gold-catalyzed isomerization of unactivated allenes into 1,3-dienes with nitrosobenzene as an additive. This reaction proceeded almost exclusively at room temperature for highly substituted allenes. The utility of this reaction is manifested by the development of one-pot [4+2]-cycloaddition of allenes and reactive alkenes.

Arylation and vinylation of alkenes based on unusual sequential semipinacol rearrangement/Grob fragmentation of allylic alcohols

(Chemical Equation Presented) Alkenes can be stereoselectively arylated and vinylated without transition-metal catalyst under mild conditions through an interesting NBS-promoted semipinacol rearrangement and a subsequent unusual NaOH-mediated Grob fragmentation.

The cross-coupling reaction of vinylindiums generated via hydroindation of terminal alkynes with diaryliodoniums salts

In InCl3-NaBH4-MeCN system, vinylindiums generated by hydroindation of aryl terminal alkynes can undergo cross-coupling reaction with diaryliodonium salts high regio- and stereoselectively. But under the same conditions, the aliphatic terminal alkynes do not react very well.

Synthesis of (E)-alkenes via hydroindation of C{triple bond, long}C in InCl3-NaBH4 system

In InCl3-NaBH4-MeCN system, terminal aryl alkynes could couple with aryl iodides and bromides to give disubstituted alkenes via hydroindation of C{triple bond, long}C. In the similar way, (E)-alkenylsilanes were synthesized via reduction of alkynylsilanes in tetrahydrofuran (THF) in high yields. The processes showed high regio- and stereoselectivity.

Heck reaction of vinyl bromides with alkenes in the presence of a tetraphosphine/palladium catalyst

Through the use of [PdCl(C3H5)]2- cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of vinyl bromides undergo Heck reaction with a wide variety of alkenes leading selectively to the corresponding 1,3-dienes in good yields. Furthermore, it can be used at low loading even for reactions of sterically hindered vinyl bromides.