6938-39-2

Usage

InChI:InChI=1/C22H27NO6/c1-12(2)16-10-15(11-17(13(3)4)20(16)24)23-29-22(25)14-8-18(26-5)21(28-7)19(9-14)27-6/h8-13H,1-7H3

Upstream product

• 71-23-8 propan-1-ol 
• 75748-09-3 (4-methoxybenzoyl)trimethylsilane 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 860178-73-0 4-ethynyl-1,2-dimethylbenzene 
• 176910-67-1 2-(4-methoxyphenylethynyl)benzaldehyde 
• 766-46-1 2-bromo-1-ethynylbenzene 
• 768-60-5 4-methoxyphenylacetylen 
• 3424-93-9 4-methoxyphenylacetamide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 2720-67-4 potassium propylxanthate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100057-36-1 1-methoxy-4-(propoxymethyl)benzene 
• 696-62-8 para-iodoanisole 
• 201230-82-2 carbon monoxide 

Relevant academic research and scientific papers

Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source

Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]

Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters

A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.

Dehydrogenative cross-coupling of primary alcohols to form cross-esters catalyzed by a manganese pincer complex

Base-metal-catalyzed dehydrogenative cross-coupling of primary alcohols to form cross-esters as major products, liberating hydrogen gas, is reported. The reaction is catalyzed by a pincer complex of earth-abundant manganese in the presence of catalytic base, without any hydrogen acceptor or oxidant. Mechanistic insight indicates that a dearomatized complex is the actual catalyst, and indeed this independently prepared dearomatized complex catalyzes the reaction under neutral conditions.

Visible light mediated oxidation of benzylic sp3 C-H bonds using catalytic 1,4-hydroquinone, or its biorenewable glucoside, arbutin, as a pre-oxidant

Benzylic ethers undergo a visible light induced C-H activation and oxygen insertion to give the corresponding benzoate esters in moderate to good yields. The conditions employ substoichiometric amounts of 1,4-hydroquinone with copper(ii) chloride dihydrate as an electron-transfer mediator, oxygen as the terminal oxidant and dimethyl carbonate as solvent under visible light irradiation. The naturally occurring glucoside, arbutin, which is commercially available or can be accessed via extraction of the leaves of bearberry (Arctostaphylos uva-ursi) or elephant ears (Bergenia crassifolia) can be used as a biorenewable source of 1,4-hydroquinone. The methodology exploits the increase in oxidizing ability of quinones upon irradiation with visible light, and offers a sustainable alternative for the late stage oxidative functionalization of benzylic C-H bonds. It is applicable to a range of cyclic benzylic ethers such as isochromans and phthalans, and simple benzyl alkyl ethers. It can also be applied in the oxidation of benzylic amines into amides, and of diarylmethanes into the corresponding ketones. Mechanistic studies suggest that the reaction proceeds by H-abstraction by the photo-excited triplet benzoquinone to give a benzylic radical that subsequently reacts with molecular oxygen.

Phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts

In this communication, an interesting phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts has been reported. At room temperature and under CO pressure, moderate to good yields of the desired esters can be produced in the absence of bases or an

Synthesis of Hydroxybenzoic Acids and Their Esters by Reaction of Phenols with Carbon Tetrachloride and Alcohols in the Presence of Iron Catalysts

Alkyl esters of hydroxy-, methoxy-, and ethoxybenzoic and cresotic acids have been synthesized by reaction of phenols, anisole, phenetole, and cresols with carbon tetrachloride and alcohols in the presence of iron catalysts.

Carbon monoxide is used as a source of halogen compound heterogeneous palladium catalyst in the presence of the aldehyde carbonyl compound by reaction carbonylation method (by machine translation)

[Problem] catalyst and the presence of carbon monoxide, the halogen compound is a carbonyl compound in the carbonylation reaction, catalysts or carbon monoxide source technique has problems. [Solution] the presence of the catalyst and the carbon monoxide, the halogen compound is carbonylation reaction method for producing a carbonyl compound, As a heterogeneous palladium catalyst, carbon monoxide is produced from an aldehyde carbonyl compound used in the method. [Drawing] no (by machine translation)

Efficient synthesis of esters through oxone-catalyzed dehydrogenation of carboxylic acids and alcohols

Since esters are important organic synthesis intermediates, an environmentally friendly oxone catalyzed-esterification of carboxylic acids with alcohols has been developed. A series of carboxylic acid esters are obtained in high yield. This strategy requires mild reaction conditions, providing an attractive alternative for the construction of valuable carbonyl esters. Electron-rich and electron-deficient groups are compatible with the standard conditions and a variety of substrates are demonstrated. Moreover, the reaction could easily be adapted to typical prodrugs, drugs and gram-scale synthesis.

Practical: In situ -generation of phosphinite ligands for palladium-catalyzed carbonylation of (hetero)aryl bromides forming esters

An effective method for alkoxycarbonylation of (hetero)aryl bromides is developed in the presence of in situ-generated phosphinite ligands tBu2POR (R = nBu, nPr, Et or Me). For this purpose commercially available tBu2PCl was used as the pre-ligand in the presence of different alcohols. For the first time cross coupling reactions with two alcohols-one generating the ligand, the other used as substrate-were developed. Through this method, ligand optimization can be performed in a more efficient manner and the desired products could be obtained with good yields and selectivity.

Zinc-Catalyzed Esterification of N-β-Hydroxyethylamides: Removal of Directing Groups under Mild Conditions

Amide transformations involving C–N bond cleavage are recognized as difficult reactions owing to the inert nature of amides resulting from resonance. Accordingly, a strong inductive effect and geometrical distortion reasonably decrease the resonance stabilization to attenuate the C–N linkage. Although the conversion of such activated amides has been studied intensively, reaction systems for “unactivated” amides are underdeveloped. We herein report that a zinc(II) trifluoromethanesulfonate [Zn(OTf)2] catalyst achieves the esterification of a wide range of unactivated tertiary amides with the assistance of intramolecular acyl rearrangement. The reaction was applied to the one-pot removal of various amide-based directing groups under mild reaction conditions to afford the corresponding esters in high yields.