17138-79-3

Upstream product

• 108-94-1 cyclohexanone 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 
• 5720-07-0 4-methoxyphenylboronic acid 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 108-93-0 cyclohexanol 

Downstream Products

• 5537-76-8 6-(4-methoxyphenyl)-6-oxohexanoic acid 
• 36263-51-1 1-(4-methoxyphenyl)cyclohexane carbonitrile 
• 613-37-6 4-methoxylbiphenyl 
• 17138-51-1 S-<1-(p-Methoxy-phenyl)-cyclohexyl>-L-cystein 
• 104-92-7 1-bromo-4-methoxy-benzene 

Relevant academic research and scientific papers

Organophotocatalytic ring opening/remote trifluoromethylselenolation of cycloalkanols

An organophotocatalytic ring opening/remote trifluoromethylselenolation of cycloalkanols is reported. This reaction proceeds the radical ring-opening in a photocatalytic system without metal catalysis under mild conditions, followed by the formation of the remote C(sp3)-SeCF3 bond in the presence of PhSO2SeCF3. The reaction brings out highly reactive to prepare trifluoromethylselenolated carbonyl compounds, suitable for a variety of aryl cyclic alcohols, while compatible with different ring systems with high yield, including 26 examples, the highest isolated yield of 93%.

Electrophotochemical Ring-Opening Bromination oftert-Cycloalkanols

An electrophotochemical ring-opening bromination of unstrainedtert-cycloalkanols has been developed. This electrophotochemical method enables the oxidative transformation of cycloalkanols with 5- to 7-membered rings into synthetically useful ω-bromoketones without the use of chemical oxidants or transition-metal catalysts. Alkoxy radical species would be key intermediates in the present transformation, which generate through homolysis of the O-Br bond in hypobromite intermediates under visible light irradiation.

Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols

The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.

Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution

The copper(I) catalyzed alkyne-azide cycloaddition (CuAAC), a click reaction, is one of the most powerful catalytic reactions developed during the last two decades. Conducting CuAAC enantioselectively would add a third dimension to this reaction and would

Enantioselective Oxy-Heck–Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (?)-Conocarpan

This work discloses the first examples of an effective enantioselective oxy-Heck–Matsuda reaction using a variety of styrenic olefins to generate chiral dihydrobenzofurans. The reaction proceeds in moderate to good yields, with high trans diastereoselectivity (up to 20:1) in enantioselectivities up to 90:10 using the N,N-ligand pyrimidine-bisoxazoline (PyriBox). The oxy-Heck–Matsuda reactions were carried out under mild conditions and rather low catalyst loadings. The feasibility and practicality of the process is demonstrated by a concise total synthesis of the neolignan (?)-conocarpan. X-ray diffraction of an advanced brominated intermediate in the route to (?)-conocarpan has allowed the unequivocal assignment of the absolute stereochemistry of the oxy-Heck–Matsuda aryldihydrobenzofuran products. A rationale for the mechanism operating in these enantioselective oxy-Heck–Matsuda reactions is also presented. (Figure presented.).

Visible-Light-Mediated Ring-Opening Strategy for the Regiospecific Allylation/Formylation of Cycloalkanols

Here we describe a straightforward and efficient approach for regiospecific introduction of an allyl group into cycloalkanol molecules employing a visible-light-mediated ring-opening strategy. A wide range of distally allylated or formylated ketones is fu

The Barbier-Grignard-Type Arylation of Ketones and Unexpected Cross-Coupling of Phenolic Ketones using Unactivated Aryl Bromides

A novel, highly versatile and efficient method has been developed for the Barbier-Grignard-type arylation of ketones and an unexpected cross-coupling of phenolic ketones was observed using unactivated bromides and magnesium in tetrahydrofuran/toluene at 96°C promoted by multicatalysts of cupric bromide (15 mol%), bismuth chloride (5 mol%) and silver bromide (10 mol%). The substituent and electronic effects on the reaction have been discussed. High yields of arylation and cross-coupling have been attained under mild conditions. A novel reasonable mechanism involving a quinone intermediate is proposed. The high chemical selectivity in the cross-coupling to the hydroxy group of phenolic ketones should help ketones find new applications.

Iodine-Promoted Metal-Free Aromatization: Synthesis of Biaryls, Oligo p-Phenylenes and A-Ring Modified Steroids

We describe efficient procedures based on the use of iodine for the synthesis of biaryls from arylcyclohexenols or arylcyclohexanols using sub-stoichiometric/catalytic iodine and dimethyl sulfoxide (DMSO) as oxidant. Heteroarylcyclohexanols also produced the corresponding biaryl products. It was proven that biphenyl can also be efficiently obtained when the quantity of iodine was reduced to 0.05 equiv. The method is compatible with different functional groups in the aromatic ring (either electron-donating or electron-withdrawing groups). For substrate scope, apart from cyclohexanone and cyclohexenone, some substituted cyclohexanones were also used to synthesize the starting arylcyclohexanols. The process was applied to the synthesis of oligo p-phenylenes and A-ring aromatized steroids, where the combined use of I2/DMSO not only provoked the necessary migration of the methyl group at C-10, but also further extended the conjugation.

Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: Development of an asymmetric aza-pinacol cyclization

The first highly enantioselective catalytic protocol for the reductive coupling of ketones and hydrazones is reported. These reactions proceed through neutral ketyl radical intermediates generated via a concerted proton-coupled electron transfer (PCET) event jointly mediated by a chiral phosphoric acid catalyst and the photoredox catalyst Ir(ppy)2(dtbpy)PF6. Remarkably, these neutral ketyl radicals appear to remain H-bonded to the chiral conjugate base of the Bronsted acid during the course of a subsequent C-C bond-forming step, furnishing syn 1,2-amino alcohol derivatives with excellent levels of diastereo- and enantioselectivity. This work provides the first demonstration of the feasibility and potential benefits of concerted PCET activation in asymmetric catalysis.

Ni-catalysed, domino synthesis of tertiary alcohols from secondary alcohols

The use of in situ generated (NHC)-Ni catalytic species (NHC = N-heterocyclic carbene) allows for the synthesis, in short reaction times, of a variety of tertiary alcohols from secondary alcohols through a domino oxidation-addition protocol.