67130-93-2

Upstream product

• 98-86-2 acetophenone 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 766-46-1 2-bromo-1-ethynylbenzene 
• 100-51-6 benzyl alcohol 
• 98-85-1 1-Phenylethanol 
• 18982-54-2 o-bromobenzyl alcohol 
• 583-55-1 1-Bromo-2-iodobenzene 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 2039-88-5 2-bromostyrene 
• 108-86-1 bromobenzene 
• 1310343-28-2 3-(2-bromophenyl)-N-methoxy-N-methylpropanamide 

Downstream Products

• 1961-97-3 3-phenyl-1H-indene 
• 36374-47-7 1-hydroxy 1-phenyl indane 
• 923595-12-4 2-(3-oxo-3-phenyl-propyl)-phenyl boronic acid 
• 1119036-73-5 1-bromo-2-(3-phenylbut-3-en-1-yl)benzene 
• 923595-11-3 2-[2-(2-bromo-phenyl)-ethyl]-2-phenyl-1,3-dioxolane 

Relevant academic research and scientific papers

Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite

Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.

BTP-Rh@g-C3N4 as an efficient recyclable catalyst for dehydrogenation and borrowing hydrogen reactions

Highly active catalysts play an important role in modern catalysis. A novel and efficient ligand benzotriazole-pyrimidine (BTP) and the corresponding rhodium composite on C3N4 were successfully synthesized. The resulting rhodium composite was fully characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), x-ray diffraction (XRD), thermogravimetric analysis (TGA), and x-ray photoelectron spectroscopy (XPS). The obtained composite exhibited good catalytic activity and good recovery performance in the synthesis of quinoxaline from 2-aminobenzyl alcohol and benzonitrile, and more than 20 quinoxalines were obtained in good yields. Additionally, it also showed that rhodium composite could achieved good catalytic performance in the synthesis of functionalized ketone through borrowing hydrogen strategy.

Iridium-catalyzed reductive etherification of α,β-unsaturated ketones and aldehydes with alcohols

An iridium complex-catalyzed reductive etherification of α,β-unsaturated ketones and aldehydes with primary alcohols is presented, affording allyl ethers in excellent yields. Deuterated and control experiments showed that this etherification transformation proceeded through a cascade transfer hydrogenation and alcohol condensation process. Moreover, the utility of this protocol is evidenced by the gram-scale performance.

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.

Lewis Acid Mediated Domino Intramolecular Cyclization: Synthesis of Dihydrobenzo[ a]fluorenes

An efficient and facile method for the regioselective synthesis of novel dihydrobenzo[a]fluorenes from readily accessible alkynols is presented. The current strategy triggers the formation of a dual C-C bond intramolecularly via Lewis acid catalysis under mild reaction conditions. Notably, secondary as well as tertiary alcohols bearing an alkyne moiety have been smoothly transformed into the corresponding products. As a result, novel tetracyclic dihydrobenzo[a]fluorenes have been accomplished using this approach.

An Access to Benzo[a]fluorenes, Benzo[b]fluorenes, and Indenes Triggered by Simple Lewis Acid

This report illustrates BF3·OEt2 promoted intramolecular cascade cycloaromatization of 1,7-ynones toward synthesizing structurally diverse benzofluorene scaffolds. Remarkably, the present protocol promotes the formation of two consecutive C-C bonds intramolecularly and undergoes aromatization under mild reaction conditions to afford the tetracyclic benzo[a]fluorene frameworks. Besides, the formation of indenes was observed when 1-bromo-2-iodoarenes are relatively more electron-rich when compared with the one originating from the terminal arylacetylenes, under controlled conditions, wherein triple bond polarity has been just reversed due to the change of electronic effects exerted by the strong +M group of 1-bromo-2-iodoarenes, which is in conjugation to the connected triple bond. The same concept to generate indenes has also been extended by using aliphatic alkyne tethered ynones. Further, it was noticed that 1,7-ynones bearing the more electron-rich 1-bromo-2-iodoarenes than the arene ring arriving from the terminal arylacetylenes lead to benzo[b]fluorenes, under thermodynamic conditions, instead of delivering the benzo[a]fluorenes. In addition, this method features metal-free conditions, easily accessible starting materials, operational simplicity, gram-scale synthesis, and a wide range of substrate scopes.

Neutral-eosin Y-catalyzed regioselective hydroacylation of aryl alkenes under visible-light irradiation

Styrene derivatives were hydroacylated with exclusive anti-Markovnikov selectivity by using neutral eosin Y as a direct hydrogen-atom-transfer (HAT) catalyst under visible-light irradiation. Aldehydes and styrenes with various substituents were tolerated (>20 examples), giving the corresponding products in moderate to high yields. The key acyl radical intermediate was generated from a direct HAT process induced by photoexcited eosin Y. Subsequent addition to styrenes and a reverse HAT process generated the ketone products.

Ligand-tuned cobalt-containing coordination polymers and applications in water

Ligands play a key role in modern catalysis research and occasionally determine whether a reaction will take place under specific conditions, such as in water. In this experiment, ligands containing an indole-based diacid moiety were employed to prepare the corresponding cobalt coordination polymer material (Co-CIA) and porous oval polymer material (Co-NCIA). Interestingly, it was observed that Co-CIA could promote the alkylation of ketones with alcohols and alcohols with alcohols, while Co-NCIA was effective for the synthesis of 1-benzyl-2-aryl-1H-benzo[d]imidazoles from various phenylenediamine and benzyl alcohols through borrowing hydrogen and dehydrogenation strategies. Other mechanism explorations, such as deuterium labeling experiments and a kinetics study, were conducted to better understand Co-CIA and Co-NCIA systems and the related transformations. Our studies provided an efficient method for the development of highly active cobalt coordination polymer materials with excellent recovery performance for dehydrogenation and borrowing hydrogen reactions under water and base-free conditions.

Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME

Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.

Nickel-catalyzed asymmetric intramolecular reductive heck reaction of unactivated alkenes

An asymmetric Ni-catalyzed intramolecular reductive Heck reaction of unactivated alkenes tethered to aryl bromides has been accomplished, providing a variety of benzene-fused cyclic compounds bearing a quaternary stereogenic center in good to excellent yi