53635-05-5

Upstream product

• 2039-87-4 2-chlorostyrene 
• 1067-87-4 Diethyl allylphosphonate 
• 89-98-5 2-chloro-benzaldehyde 
• 1794-45-2 2-chlorocinnamaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1560-54-9 allyltriphenylphosphonium bromide 

Downstream Products

• 1794-45-2 (E)-3-(2-chlorophenyl)propenal 

Relevant academic research and scientific papers

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.

Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides

A highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides has been realized by using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand. The reaction provided an efficient approach to synthetically useful chiral allylic sulfones. Mechanistic studies suggest that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product. The transformation of the allyl hydrazine intermediate to the product is the enantioselectivity-determining step.

Design of 1,2-dioxines with anti-Candida activity: aromatic substituted 1,2-dioxines

In an ongoing effort to rationally design new antimicrobials, 47 new 1,2-dioxines have been synthesised. Broad antifungal structure-activity relationships governing aromatically substituted epoxy-1,2-dioxines 2 and 3 and their parent 1,2-dioxines 1 were a

Process for dimerization, arylation and trifluoromethylation of aromatic and heterocyclic compounds

A decarboxylation process for coupling aromatic compounds wherein cyclic hydrocarbons and heterocyclic compounds having at least one labile ring hydrogen are reacted with the mono silver salts of aromatic carboxylic acids, or mono silver salts of unsaturated compounds such as α,β-ethylenically unsaturated acid compounds, or silver trifluoroacetate, or the mono silver salts are reacted with themselves, by heating to temperatures of 100° to 500° C. at pressures of 0.1 to 10 atmospheres, or by irradiating the reactants with ultraviolet light of 200 to 400 nanometers at temperatures of -30° to 150° C. The resulting dimers, trimers, polysubstituted polyphenyls, polyheterocyclics and trifluoromethylated aromatics are useful as heat transfer media, as intermediates for high molecular weight polymers, pesticides and petroleum additives, and as scintillation counters.