18138-77-7

Upstream product

• 109-99-9 tetrahydrofuran 
• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 103-64-0 bromostyrene 
• 637-44-5 phenylpropyolic acid 
• 16874-33-2 tetrahydro-2-furancarboxylic acid 
• 176312-30-4 (E)-2-iodo-2-phenyl-1-ethenyl trifluoromethyl sulfone 
• 69936-53-4 6-phenylhex-5-yn-1-ol 
• 1394313-89-3 6-phenylhex-5-yne-1,4-diol 
• 1394313-42-8 (E)-1-phenylhex-2-ene-1,6-diol 
• 59700-95-7 (E)-6-phenylhex-5-ene-1,4-diol 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-96-5 (2-nitroethenyl)benzene 

Downstream Products

• 1318799-85-7 (E)-triethyl(6-phenyl-4-vinylhex-5-enyloxy)silane 

Relevant academic research and scientific papers

Synthesis of styryl tetrahydrofurans and tetrahydropyrans via addition of radicals to unsaturated sulfimides

The addition of tetrahydrofuranyl or tetrahydropyranyl radicals to (E)-styryl sulfimide derivatives furnishes the corresponding (E)-styryl tetrahydrofurans or tetrahydropyrans respectively. The corresponding radical reactions with (Z)-styryl sulfimides gives rise to a mixture of (E) and (Z) isomers, this is in contrast to the Et3B mediated reaction, which is stereoselective.

Direct, Site-Selective and Redox-Neutral α-C?H Bond Functionalization of Tetrahydrofurans via Quantum Dots Photocatalysis

As one of the most ubiquitous bulk reagents available, the intrinsic chemical inertness of tetrahydrofuran (THF) makes direct and site-selective C(sp3)?H bond activation difficult, especially under redox neutral condition. Here, we demonstrate that semiconductor quantum dots (QDs) can activate α-C?H bond of THF via forming QDs/THF conjugates. Under visible light irradiation, the resultant alkoxyalkyl radical directly engages in radical cross-coupling with α-amino radical from amino C?H bonds or radical addition with alkene or phenylacetylene, respectively. In contrast to stoichiometric oxidant or hydrogen atom transfer reagents required in previous studies, the scalable benchtop approach can execute α-C?H bond activation of THF only by a QD photocatalyst under redox-neutral condition, thus providing a broad of value added chemicals starting from bulk THFs reagent.

Decarboxylative Hydroalkylation of Alkynes via Dual Copper-Photoredox Catalysis

A photoredox strategy for the synthesis of a wide range of allylic amines and ethers from carboxylic acids and alkynes has been developed. This approach relies on the perturbation of the ground-state electronic properties of terminal alkynes through the formation and photoexcitation of copper acetylide intermediates. This process takes place through cooperative copper and organic photoredox catalysis and can be carried out in a stereodivergent manner. Thus, a systematic multivariate HTE screening spotlighted that a switch in the stereochemical outcome can be provoked by choosing an appropriate combination of ligand and base. The developed methodology has been applied to the stereoselective coupling of primary, secondary, and tertiary alkyl radicals with (hetero)aromatic terminal alkynes. As an additional practicality, similar reaction conditions allowed for the use of aromatic amines as radical precursors in a cross dehydrogenative coupling for the direct vinylation of inactivated C-H bonds.

Phenylglyoxylic Acid: An Efficient Initiator for the Photochemical Hydrogen Atom Transfer C?H Functionalization of Heterocycles

C?H functionalization at the α-position of heterocycles has become a rapidly growing area of research. Herein, a cheap and efficient photochemical method was developed for the C?H functionalization of heterocycles. Phenylglyoxylic acid (PhCOCOOH) could behave as an alternative to metal-based catalysts and organic dyes and provided a very general and wide array of photochemical C?H alkylation, alkenylation, and alkynylation, as well as C?N bond forming reaction methodologies. This novel, mild, and metal-free protocol was successfully employed in the functionalization of a wide range of C?H bonds, utilizing not only O- or N-heterocycles, but also the less studied S-heterocycles.

Photoredox Oxo-C(sp3)-H Bond Functionalization via in Situ Cu(I)-Acetylide Catalysis

A unified strategy for the synthesis of 2-vinyl heterocycles is reported. With visible light irradiation, simple and cheap CuCl is able to functionalize a terminal alkyne, giving Cu(I)-acetylide in situ. Unlike the case of noble metals or organic dye photocatalysts, this critical Cu(I)-acetylide not only activates the C-H bond of terminal alkynes but also serves as a photocatalyst to achieve varieties of 2-vinyl heterocycles in good to excellent yields, even for large scale and late-stage functionalization of natural product.

Synthesis of Chiral Bifunctional NHC Ligands and Survey of Their Utilities in Asymmetric Gold Catalysis

The synthesis and characterization of the chiral bifunctional NHC ligands based on the imidazo[1,5-a]pyridine (ImPy) scaffold are described. These ligands possess a fluxional biaryl axis and a chiral center. The configurational stability of the biaryl axis in their gold(I) complexes is investigated. The application of these axially chiral ImPy-based AuCl complexes in a series of gold catalysis is explored, and varying degrees of asymmetric induction are observed. In most cases, the ligand (aS,R)-L8-H with its cyclohexyl group pointing to the reaction site and hence exerting asymmetric steric influence is more effective in asymmetric induction.

Method for synthesizing cis-olefin by catalyzing decarboxylation coupling reaction of NHP ester and aryl-terminated alkyne with iridium

The invention provides a method for synthesizing Z-selective olefin by catalyzing a decarboxylation coupling reaction of an NHP ester and aryl-terminated alkyne with iridium. The aryl-terminated alkyne and its derivative and the NHP ester undergo a one-po

Selective Syntheses of Z-Alkenes via Photocatalyzed Decarboxylative Coupling of N-Hydroxyphthalimide Esters with Terminal Arylalkynes

A novel, efficient Z-alkene synthesis via photocatalyzed decarboxylative couplings between terminal aryl alkynes and alkyl N-hydroxyphthalimide (NHPI) esters, which are derived from aliphatic carboxylic acids, is described. A wide range of primary, secondary, and tertiary carboxylates as well as α-amino acid and α-oxyacid-derived esters were employed as suitable substrates. The mild reaction conditions, broad substrate scope, functional group tolerance, and operational simplicity make this decarboxylative coupling reaction a valuable method in organic syntheses.

NiCl2-catalyzed radical cross decarboxylative coupling between arylpropiolic acids and cyclic ethers

A direct alkenylation of cyclic ethers via radical cross decarboxylative coupling process catalyzed by NiCl2 and using DTBP as radical initiator and oxidant was developed. A variety of arylpropiolic acids and cyclic ethers were transformed into the corresponding 2-arylvinyl cyclic ethers in moderate to excellent yields. Mechanistic experiments were conducted to determine the nature of the reaction intermediates, and a plausible reaction mechanism involving NiCl2-promoted radical process was proposed.

Visible Light Mediated C(sp3)-H Alkenylation of Cyclic Ethers Enabled by Aryl Ketone

C?H alkenylation of cyclic ethers (THF, 1,4-dioxane) using the readily available nitroalkenes as the alkenylating reagents has been developed. It allows the rapid access to the α-alkenyl ethers with high E-selectivity. The previous inaccessible α-dienyl e