34599-75-2

Upstream product

• 21564-79-4 2-methyl-1,2-dihydronaphthalene 
• 79265-88-6 1-propen-2-yl-1,3-dihydrobenzothiophen 2,2-dioxide 
• 91-13-4 α,α'-dibromo-o-xylene 
• 1097191-50-8 1-allyl-2-(2-methylbenzyliene)hydrazine 
• 4549-82-0 (E)-2-methylcinnamaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1250596-10-1 1-(o-tolyl)but-3-yn-1-ol 
• 6502-18-7 1-(but-3-yn-1-yl)-2-methylbenzene 
• 95-46-5 2-methylphenyl bromide 
• 1560-54-9 allyltriphenylphosphonium bromide 
• 529-20-4 2-methylphenyl aldehyde 
• 41301-43-3 trimethyl-2-propen-1-ylphosphonium bromide 
• 24165-62-6 1-(2-methylphenyl)but-3-en-1-ol 
• 20850-01-5 3-(2-methylphenyl)-2-propen-1-ol 

Downstream Products

• 1352922-03-2 1-[(1E,3E)-6,7-dimethylocta-1,3,6-trien-1-yl]-2-methylbenzene 
• 1352922-19-0 1-methyl-2-((E)-5,6-dimethyl-3-methylenehepta-1,5-dienyl)benzene 
• 3695-02-1 N-benzyl-N-methyl-p-toluenesulfonamide 

Relevant academic research and scientific papers

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

Nickel-catalyzed allyl-allyl coupling reactions between 1,3-dienes and allylboronates

A regiospecific allyl-allyl coupling reaction between 1,3-dienes and allylboronates has been demonstrated under nickel catalysis. Salient features of this method include the earth-abundant metal catalyst, excellent regioselectivity and good functional group tolerance. Notably, even congested allyl substrates can also be applied to this protocol, thus allowing for the rapid preparation of a series of valuable 1,5-dienes. This journal is

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.

Boron-Catalyzed C?C Functionalization of Allyl Alcohols

Tris(pentafluorophenyl)borane-catalyzed C?C bond functionalization of arylallyl alcohols using donor-acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method can also be employed to effect homologation of allyl alcohols to homoallyl alcohols. Overall, this metal-free transformation presents a novel disconnection strategy towards carbon-carbon bond scission and formation. (Figure presented.).

Boron-catalyzed CC functionalization of allyl alcohols

Tris(pentafluorophenyl)borane-catalyzed CC bond functionalization of arylallyl alcohols using donor-acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method can also be employed to effect homologation of allyl alcohols to homoallyl alcohols. Overall, this metal-free transformation presents a novel disconnection strategy towards carbon-carbon bond scission and formation.

Tandem Cyclopropanation/Vinylogous Cloke-Wilson Rearrangement for the Synthesis of Heterocyclic Scaffolds

Cyclopropanation of 1,3-dienes with ethyl 2-formyldiazoacetate under rhodium catalysis results in either a tandem cyclopropanation/Cloke-Wilson rearrangement or a vinylogous variant, depending on the diene used. These adducts may be subjected to an oxygen

Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO2

A site-selective catalytic incorporation of multiple CO2 molecules into 1,3-dienes en route to adipic acids is described. This protocol is characterized by its mild conditions, excellent chemo- and regioselectivity and ease of execution under CO2 (1 atm), including the use of bulk butadiene and/or isoprene feedstocks.

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.