77605-17-5

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 563-57-5 3,3-dichloropropene 
• 80227-73-2 1-phenyl-4-hexen-3-ol 
• 504-60-9 penta-1,3-diene 
• 100-44-7 benzyl chloride 
• 591-93-5 1,4-Pentadiene 
• 956430-56-1 (1R,2S,7S)-4-[(Z)-3-(dimethyl(phenyl)silanyl)allyl]-1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.0^2,6]decane 
• 50876-48-7 (2Z)-penta-2,4-dienyl-N,N-dimethylamine 
• 91788-88-4 allyl-triethylphosphonium-bromide 
• 156701-45-0 2-(prop-2-enylsulfonyl)benzothiazole 
• 273730-83-9 1-phenyl-5-(prop-2'-ene-1'-sulfonyl)-1H-tetrazole 
• 53722-76-2 diallyldiphenylarsonium bromide 
• 41923-73-3 methyl (prop-2-enyl)diphenylarsonium iodide 
• 53915-69-8 allenyltributylstannane 

Downstream Products

• 77605-26-6 (1R,2S)-2-Phenethyl-cyclopent-3-enol 
• 77605-18-6 {(Z)-4-[(1S,2R)-2-(2-Chloro-ethoxy)-cyclopropyl]-but-3-enyl}-benzene 
• 77605-18-6 {(Z)-4-[(1S,2S)-2-(2-Chloro-ethoxy)-cyclopropyl]-but-3-enyl}-benzene 
• 851592-02-4 (4R)-2,2-dimethyl-4-[(1Z)-4-phenylbut-1-enyl]-1,3-dioxolane 
• 851592-07-9 (3Z)-(2S)-6-phenylhex-3-ene-1,2-diol 
• 1588-44-9 6-phenyl-1-hexene 
• 1347759-82-3 N-p-nitrobenzenesulfonyl-2-(2-phenylethyl)-3-pyrroline 
• 39669-95-9 (E)-hexa-3,5-dien-1-ylbenzene 
• 1625639-71-5 C₁₄H₁₈ 
• 1625639-69-1 C₁₄H₁₈ 

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

Copolymerization of 1,3-butadiene with phenyl/phenethyl substituted 1,3-butadienes: a direct strategy to access pendant phenyl functionalized polydienes

Copolymerization of 1,3-butadiene with various types of phenyl substituted 1,3-butadiene derivatives, including (E)-1-phenyl-1,3-butadiene (PBD), 1-phenethyl-1,3-butadiene (PEBD), 1-(4-methoxylphenyl)-1,3-butadiene (p-MEPBD), 1-(2-methoxylphenyl)-1,3-buta

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 Copper-Catalyzed Asymmetric C-O Cross-Coupling

The construction of carbon-heteroatom bonds is one of the most active areas of research in organic chemistry because the function of organic molecules is often derived from the presence of heteroatoms. Although considerable advances have recently been achieved in radical-involved catalytic asymmetric C-N bond formation, there has been little progress in the corresponding C-O bond-forming processes. Here, we describe a photoinduced copper-catalyzed cross-coupling of readily available oxime esters and 1,3-dienes to generate diversely substituted allylic esters with high regio- and enantioselectivity (>75 examples; up to 95% ee). The reaction proceeds at room temperature under excitation by purple light-emitting diodes (LEDs) and features the use of a single, earth-abundant copper-based chiral catalyst as both the photoredox catalyst for radical generation and the source of asymmetric induction in C-O coupling. Combined experimental and density functional theory (DFT) computational studies suggest the formation of π-allylcopper complexes from redox-active oxime esters as bifunctional reagents and 1,3-dienes through a radical-polar crossover process.

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.

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.

Cu-Catalyzed highly regioselective 1,2-hydrocarboxylation of 1,3-dienes with CO2

A practical copper-catalyzed highly regioselective 1,2-hydrocarboxylation of terminal 1,3-diene with carbon dioxide has been developed. Under mild reaction conditions, this chemistry afforded 2-benzyl-β,γ-unsaturated acid derivatives as products, which are a kind of important unit for bio-active molecules and versatile precursors for organic synthesis, with good functional group tolerance. The key intermediate in this transformation is illustrated by control experiments.

Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes

A family of single-component iron precatalysts for the [4+4]-cyclodimerization and intermolecular cross-[4+4]-cycloaddition of monosubstituted 1,3-dienes is described. Cyclooctadiene products were obtained with high regioselectivity, and catalyst-controlled access to either cis- or trans-diastereomers was achieved using 4-substituted diene substrates. Reactions conducted either with single-component precatalysts or with iron dihalide complexes activated in situ proved compatible with common organic functional groups and were applied on multigram scale (up to >100 g). Catalytically relevant, S = 1 iron complexes bearing 2-(imino)pyridine ligands, (RPI)FeL2 (RPI = [2-(2,6-R2-C6H3-Na-CMe)-C5H4N] where R = iPr or Me, L2 = bis-olefin), were characterized by single-crystal X-ray diffraction, M??bauer spectroscopy, magnetic measurements, and DFT calculations. The structural and spectroscopic parameters are consistent with an electronic structure description comprised of a high spin iron(I) center (SFe = 3/2) engaged in antiferromagnetically coupling with a ligand radical anion (SPI = -1/2). Mechanistic studies conducted with these single-component precatalysts, including kinetic analyses, 12C/13C isotope effect measurements, and in situ M??bauer spectroscopy, support a mechanism involving oxidative cyclization of two dienes that determines regio- and diastereoselectivity. Topographic steric maps derived from crystallographic data provided insights into the basis for the catalyst control through stereoselective oxidative cyclization and subsequent, stereospecific allyl-isomerization and C-C bond-forming reductive elimination.

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

Rhodium-Catalyzed Annulations of 1,3-Dienes and Salicylaldehydes/2-Hydroxybenzyl Alcohols Promoted by 2-Ethylacrolein

A rhodium-catalyzed 2-ethylacrolein-promoted protocol enables the annulation reactions of 1,3-dienes with either salicylaldehydes or 2-hydroxybenzyl alcohols leading to 2-alkylchroman-4-ones with high regioselectivity. This research highlights the use of 2-ethylacrolein which probably serves as a tool of bidentate coordination to rhodium intermediates. Mechanistic studies reveal that the transformation proceeds through the 1,4-hydroacylation pathway to access unsaturated linear ketones with subsequent oxo-Michael addition. (Figure presented.).