73110-53-9

Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 90-01-7 salicylic alcohol 
• 66715-21-7 2-p-tolyl-4H-chromene 
• 1009633-73-1 (R)-3-iodo-1-(4-methylphenyl)-1-propanol 
• 95-56-7 2-hydroxybromobenzene 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 18982-54-2 o-bromobenzyl alcohol 
• 122-00-9 para-methylacetophenone 
• 1329810-25-4 3-(2-hydroxyphenyl)-1-p-tolylpropan-1-one 
• 7645-95-6 2-hydroxy-4'-methyl-chalcone 
• 90-02-8 salicylaldehyde 

Relevant academic research and scientific papers

One pot tandem dual CC and CO bond reductions in the β-alkylation of secondary alcohols with primary alcohols by ruthenium complexes of amido and picolyl functionalized N-heterocyclic carbenes

Two different classes of ruthenium complexes, namely, [1-mesityl-3-(2,6-Me2-phenylacetamido)-imidazol-2-ylidene]Ru(p-cymene)Cl (1c) and {[1-(pyridin-2-ylmethyl)-3-(2,6-Me2-phenyl)-imidazol-2-ylidene]Ru(p-cymene)Cl}Cl (2c), successfully catalyzed the one-pot tandem alcohol-alcohol coupling reactions of a variety of secondary and primary alcohols, in moderate to good yields of ca. 63-89%. The mechanistic investigation performed on two representative catalytic substrates, 1-phenylethanol and benzyl alcohol using the neutral ruthenium (1c) complex showed that the catalysis proceeded via a partially reduced CC hydrogenated carbonyl species, [PhCOCH2CH2Ph] (3′), to the fully reduced CO and CC hydrogenated secondary alcohol, [PhCH(OH)CH2CH2Ph] (3). Furthermore, the time dependent study showed that the major product of the catalysis modulated between (3′) and (3) during the catalysis run performed over an extended period of 120 hours. Finally, the practical utility of the alcohol-alcohol coupling reaction was demonstrated by preparing five different flavan derivatives (13-17) related to various bioactive flavonoid natural products, in a one-pot tandem fashion.

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl3/Et3SiH System by Switching the Solvent

An efficient one-pot synthesis of O-heterocycles or aryl ketones has been achieved using Et3SiH in the presence of InCl3 via a sequential ionic hydrogenation reaction by switching the solvent. This methodology can be used to construct C-O bonds and to prepare conjugate reduction products, including chromans, tetrahydrofurans, tetrahydropyrans, dihydroisobenzofurans, dihydrochalcones, and 1,4-diones in a facile manner. In addition, a novel plausible mechanism involving a conjugate reduction and a tandem reductive cyclization was verified by experimental investigations.

Tandem Cross Coupling Reaction of Alcohols for Sustainable Synthesis of β-Alkylated Secondary Alcohols and Flavan Derivatives

A Ru(II) NHC complex (loading down to 0.001 mol%) catalyzed cross coupling of a broad range of aromatic, aliphatic and heterocyclic alcohols is reported. This protocol also functioned efficiently under solvent-free conditions. Remarkably, this catalytic system disclosed so far the highest TON of 288000 for the cross coupling of alcohols. Notably, this methodology was successfully applied for the one-pot synthesis of a range of flavan derivatives. A detailed DFT studies and kinetic experiments were performed to understand the reaction mechanism as well as the high reactivity of this catalytic system. (Figure presented.).

One step synthesis of 2-alkenylchromanes via inverse electron-demand Hetero-Diels–Alder reaction of o-quinone methide with unactivated dienes

The synthetically important 2-alkenylchromane derivatives were constructed in good yields under metal-free condition via inverse electron demand Hetero-Diels–Alder reaction of o-quinone methides with unactivated dienes. This strategy features mild conditi

Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: Synthesis of 2-arylchromans

Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable.

Enantioselective synthesis of chromanes by iridium-catalyzed asymmetric hydrogenation of 4H-chromenes

Iridium complexes of chiral oxazoline-based P,N-ligands proved to be efficient catalysts for the enantioselective hydrogenation of 2-aryl- and 2-alkyl-4H-chromenes. The best results were obtained with a ligand derived from threonine (ThrePHOX), which induced ee values of 95% to >99% in the hydrogenation of 2-methyl-, 2-cyclohexyl- and various 2-aryl-substituted chromenes. Georg Thieme Verlag Stuttgart.

Asymmetric dehydration of β-hydroxy esters and application to the syntheses of flavane derivatives

Catalytic asymmetric dehydration of β-aryl or alkyl substituted β-hydroxy esters via kinetic resolution has been investigated. A brief survey of 10 different chiral ligands is conducted to examine the effects of chiral ligand structure on selectivity of t

Montmorillonite-mediated hetero-Diels-Alder reaction of alkenes and o-quinomethanes generated in situ by dehydration of o-hydroxybenzyl alcohols

The intermolecular hetero-Diels-Alder reaction of in situ-generated o-quinomethanes and unactivated alkenes has been accomplished through a wet montmorillonite catalyst in a LiClO4-MeNO2 solution to give good yields of varied chromane skeletons.

Photocyclization of 2-cinnamylphenols via excited state proton transfer (ESPT) involving the lowest-lying styrenic singlet

The attachment of substituents to the styrenic ring of trans-2-cinnamylphenol produces a decrease in the singlet energy of the styrenic moiety. As a consequence, the resulting chromophore becomes responsible for the photophysical and photochemical properties of this type of bichromophoric compounds. Both fluorescence emission and photocyclization occur predominantly from the lowest-lying styrenic singlet. The result is a marked regioselectivity towards 6-membered ring products, via an excited state proton transfer.