The direct, by-product-free conversion of basic feedstocks to products medicinal and agricultural relevance is a broad goal chemical research. Butadiene product petroleum cracking produced on an enormous scale (about 12 × 10(6) metric tons annually). Here, with the use ruthenium catalyst modified by chiral phosphate counterion, we report direct redox-triggered carbon-carbon coupling alcohols butadiene form carbonyl crotylation high levels anti-diastereoselectivity enantioselectivity in...

The ruthenium catalyst generated in situ from H2Ru(CO)(PPh3)3, (S)-SEGPHOS, and a TADDOL-derived phosphoric acid promotes butadiene hydrohydroxyalkylation to form enantiomerically enriched products. Notably, the observed diastereo- enantioselectivity is opposite of that using BINOL-derived phosphate counterions combination with same enantiomer chiral ligand. Match/mismatch effects between ligand TADDOL-phosphate counterion are described. For first time, single-crystal X-ray diffraction data...

A cationic palladium complex bearing 1,10-phenanthroline ligand is found to catalyze direct C–H arylation reactions of heteroarenes with aryl iodides give mono-, di-, or tri-arylated products selectively.

Direct triarylation and sequential reactions of simple azoles catalyzed by [Pd(phen)2]PF6 are described. Simple azoles, such as N-methylimidazole, thiazole, oxazole, were observed to undergo triaryaltion even at their C4 positions when treated with aryl iodides in the presence a catalyst stoichiometric amount Cs2CO3 DMA 150 °C. Using excess amounts selective C5 monoarylation was achieved using same catalytic system. Subsequent efforts demonstrated that arylated exclusive C2 arylation...

Oxidative condensation−cyclization of aldehydes and aryl-2-pyridylmethylamines proceeded in the presence a stoichiometric amount elemental sulfur as an oxidant absence catalyst. The reaction gave variety 1,3-diarylated imidazo[1,5-a]pyridines good to high yields. products showed fluorescence emission wavelength range 454−524 nm. quantum yields imidazopyridines were greatly improved compared those parent 3-monosubstituted compounds.

Iodine-mediated, oxidative desulfurization promoted cyclization of N-2-pyridylmethyl thioamides serves as an efficient and versatile method for the preparation 2-azaindolizines (imidazo[1,5-a]pyridines) rare 2-azaindolizine sulfur-bridged dimers. The prepared in this manner are readily converted to a variety fluorescent compounds by using transition-metal-catalyzed cross-coupling reactions.

Abstract The reactions of aromatic compounds and elemental chalcogens catalyzed by a copper salt with molecular oxygen as an oxidant were carried out. reaction 3‐substituted imidazo[1,5‐ ]pyridines sulfur in the presence CuTC (copper(I) thiophenecarboxylate) gave corresponding bisimidazopyridyl sulfides good to quantitative yields. proceeded even under aerobic oxidation conditions. use polar solvent was crucial for reaction, DMSO (dimethyl sulfoxide) particular stimulated reaction. could be...

We report an efficient method for the synthesis of pyrrolo[2,1-a]isoquinoline derivatives using sequential [3 + 2] cycloaddition/oxidative aromatization reactions catalyzed by methylene blue with fluorescent light irradiation under oxygen atmosphere. The products were obtained in moderate to good yields.

A novel cross-dehydrogenative C(sp2)–H amination catalyzed by an organic photocatalyst is reported. The reaction mediated 2-tert-butylanthraquinone as a photocatalyst, harmless visible light, and aerobic oxygen the sole oxidant without transition-metal catalyst or external oxidant.

A novel photocatalysis to construct the 3-acyl-4-arylcoumarin framework from simple aldehyde with ynoate is described. The reaction proceeded through an acyl radical intermediate generated by hydrogen atom abstraction aldehyde, followed and then cyclization afford coumarins. This valuable gave over 20 coumarin derivatives in moderate good yields inexpensive 2-tBu-anthraquinone as a catalyst. In addition, synthetic coumarins were investigated for 5α-dihydrotestosterone (DHT)-induced secretion...

Although organic-based photocatalysts provide an inexpensive, environmentally friendly alternative, many are incapable of absorption within the visible wavelength range; this ultimately influences their effectiveness. Photocatalytic reactions usually proceed via single electron transfer (SET) or energy (ET) processes from photoexcited molecules to various substrates. In our study, carbohalogenation olefins was accomplished by combining CBr4 and 4-Ph-pyridine under irradiation. The atom...

This study investigates the photoinduced C-X borylation reaction of aryl halides by forming a halogen-bonding (XB) complex using 2-naphthol as an XB acceptor. The method is chemoselective and broadly functional group tolerant provides concise access to corresponding boronate esters. Mechanistic studies reveal that between halide naphthol acts electron donor-acceptor furnish radicals through transfer.

1-Alkynyl- and 1-alkenyl-3-arylimidazo[1,5-a]pyridines were synthesized. The Sonogashira coupling of 3-aryl-1-iodoimidazo[1,5-a]pyridines various terminal alkynes with Pd(PPh(3))(2)Cl(2) (10 mol %) CuI in triethylamine at 80 °C for 12 h afforded the corresponding good to excellent yields. Mizoroki-Heck reaction styrene derivatives proceeded smoothly Pd(OAc)(2) (5 %), IMes·HCl Cs(2)CO(3) (2 equiv) DMA 130 20 give alkenylated imidazo[1,5-a]pyridines moderate high fluorescence maxima quantum...

Synthetic methods for triarylated azoles containing three different aryl groups via one-pot sequential multiple C–H bond arylations are described. The diarylation of C5-monoarylated was achieved by the simple addition two iodides with a [Pd(phen)2]PF6 catalytic system. triarylation N-methylimidazole combination previously reported Pd(OAc)2–P(2-furyl)3 system and present In this case, portionwise halide, base catalyst in final step significantly improved overall yield desired product. These...

The direct approach: Ruthenium(0)-catalyzed hydrohydroxyalkylation of α-olefins and styrenes with 3-hydroxy-2-oxindoles forms branched products CC coupling high levels diastereocontrol. A mechanism involving diene–olefin oxidative a subsequent carboxylic acid co-catalyzed transfer hydrogenolysis the resulting oxaruthenacycle intermediate is postulated. α-Olefins are abundant petrochemical feedstocks used in manufacture diverse chemical products.1 Despite their commercial significance,...

The ruthenium catalyst derived from Ru3(CO)12 and triphos [Ph2P(CH2CH2PPh2)2] promotes the direct C–C coupling of isoprene with aryl substituted hydantoins 1a–1f at diene C4-position to furnish products n-prenylation 2a–2f. A mechanism involving hydantoin dehydrogenation followed by diene-imine oxidative a transient aza-ruthencyclopentene is proposed.

Abstract Direct functionalization of the ubiquitous CH bond is receiving much attention because complex structures can be formed from simple precursors. This paper reports a useful method for direct hydroxylation 2‐phenylpyridines using palladium(II) chloride and aqueous hydrogen peroxide. In this method, peroxide, which has high atom efficiency, employed as oxidant phenol derivatives are generated via activation. magnified image

A metal-free photo-oxidative intermolecular C-H/C-H coupling reaction of thiophenes is demonstrated with carbonyls using a catalytic amount molecular iodine. In this system, oxygen in the air acted as terminal oxidant to regenerate mechanistic study was also performed.

We disclose a novel and efficient synthesis of 2-substituted quinazolines by aerobic photooxidative reaction catalyzed magnesium iodide.

Extracellular superoxide dismutase (EC-SOD) is one of the main SOD isozymes and plays an important role in prevention cardiovascular diseases by accelerating dismutation reaction superoxide. Royal jelly includes 10-hydroxy-2-decenoic acid (10H2DA, 2), which regulates expression various types genes epigenetics through effects histone deacetylase (HDAC) antagonism. The EC-SOD was previously reported to be regulated epigenetically acetylation THP-1 cells. Therefore, we herein evaluated royal...

The treatment of an O-(4-methoxybenzyl) oxime ether bearing olefin substituent and 1-chloroanthraquinone (1-Cl-AQN) catalyst in 2-butanone under visible-light irradiation affords pyrroline via iminyl radical intramolecular hydroimination. Mechanistic studies indicate that generation mainly proceeds by hydrogen abstraction the photocatalyst from benzyl position oxime. Moreover, atom was identified circulation benzylic substrates between AQN to quench carbon without requiring any additional reagents.