25203-83-2

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 762-72-1 allyl-trimethyl-silane 
• 75-77-4 chloro-trimethyl-silane 
• 115579-47-0 (allyl)(diethylamino)dimethylsilane 
• 67-63-0 isopropyl alcohol 
• 2741-38-0 allyldiphenylphosphine 
• 4141-48-4 allyldiphenylphosphine oxide 
• 1067-87-4 Diethyl allylphosphonate 
• 466672-31-1 (Z)-(1-cyclohexyl-buta-1,3-diene-2-sulfonyl)-benzene 
• 466672-30-0 (E)-(1-cyclohexyl-buta-1,3-diene-2-sulfonyl)-benzene 
• 2550-36-9 Cyclohexylmethyl bromide 
• 109-72-8 n-butyllithium 
• 13361-64-3 trimethyl(propargyl)silane 
• 108-85-0 1-bromocyclohexane 

Downstream Products

• 25203-84-3 (Z)-buta-1,3-dien-1-ylcyclohexane 
• 1599472-42-0 C₁₂H₂₀ 
• 1599472-41-9 C₁₂H₂₀ 

Relevant academic research and scientific papers

Visible-Light-Induced, Palladium-Catalyzed 1,4-Difunctionalization of 1,3-Dienes with Bromodifluoroacetamides

A highly modular 1,4-difunctionalization of 1,3-dienes with bromodifluoroacetamides and sulfinates/amines through a photoinduced palladium-catalyzed radical relay process is described herein. This developed protocol offers a facile and general route to ac

Nickel-Catalyzed Carboxylation of Conjugated Dienes with Carbon Dioxide and DIBAL-H for the Synthesis of β,γ-Unsaturated Carboxylic Acids

Conjugated dienes underwent Ni-catalyst-promoted 1,2-hydrocarboxylation in a 1:1 ratio with carbon dioxide under atmospheric pressure in the presence of diisobutylaluminum hydride (DIBAL-H) to give the corresponding β,γ-unsaturated carboxylic acids, without dimerization or oligomerization of the conjugated diene.

Selective 1,2-Aminoisothiocyanation of 1,3-Dienes Under Visible-Light Photoredox Catalysis

Selective three-component 1,2-diamination of 1,3-dienes with concurrent introduction of two orthogonally protected amino groups remains unknown despite its significant synthetic potential. We report herein that reaction of conjugated dienes with N-aminopy

Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and beyond

A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and stereoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative π-allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its application for derivatization of several amine-containing drugs.

Enantioselective Synthesis of Functionalized Arenes by Nickel-Catalyzed Site-Selective Hydroarylation of 1,3-Dienes with Aryl Boronates

A catalytic method for the site-selective and enantioselective synthesis of functionalized arenes by the intermolecular hydroarylation of terminal and internal 1,3-dienes with aryl pinacolato boronates is reported. The reactions are promoted by 5.0 mol %

Corrigendum: Up the Hill: Selective Double-Bond Isomerization of Terminal 1,3-Dienes towards Z-1,3-Dienes or 2Z,4E-Dienes (Angewandte Chemie International Edition, (2012), 51, 5, (1270-1273), 10.1002/anie.201107512)

Several years ago the authors reported an isomerisation of E-1,3-dienes by a cobalt catalyst into Z-1,3-dienes in this Communication (Scheme —original scheme). Scheme (Figure presented.) Double bond isomerisation for the stereoselective generation of Z-4

Nickel(0)-Catalyzed Hydroalkylation of 1,3-Dienes with Simple Ketones

We developed a highly regioselective addition of 1,3-dienes with simple ketones by nickel-hydride catalyst bearing DTBM-SegPhos ligand. A wide range of aromatic and aliphatic ketones directly coupled with 1,3-dienes, providing synthetically useful γ,δ-unsaturated ketones in high yield and regioselectivity. The asymmetric version of the reaction was also realized in high enantioselectivity by using novel chiral ligand DTBM-HO-BIPHEP. The utility of this hydroalkylation was demonstrated by facile product modification and enantioselective synthesis of (R)-flobufen.

Palladium-Catalyzed Chemoselective Protodecarboxylation of Polyenoic Acids

Conditions for the first palladium-catalyzed chemoselective protodecarboxylation of polyenoic acids to give the desired polyenes in good yields are presented. The reactions proceed under mild conditions using either a Pd(0) or Pd(II) catalyst and tolerate a variety of aryl and aliphatic substitutions. Unique aspects of the reaction include the requirement of phosphines, water, and a polyene adjacent to the carboxylic acid.

Catalyst Controlled Regiodivergent Arylboration of Dienes

A method for the regiodivergent arylboration of dienes is presented. These reactions allow for the formation of a diverse range of synthetically versatile products from simple precursors. Through mechanistic studies, these reactions likely operate by init

Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst

We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active catalyst but also is critical for achieving high site selectivity in the transformation.