Copper-Catalyzed Oxidative C–O Bond Formation of 2-Acyl Phenols and 1,3-Dicarbonyl Compounds with Ethers: Direct Access to Phenol Esters and Enol Esters

Park, Jihye; Han, Sang Hoon; Sharma, Satyasheel; Han, Sim-Hee; Shin, Youngmi; Mishra, Neeraj Kumar; Kwak, Jong Hwan; Lee, Cheong Hoon; Lee, Jeongmi; Kim, In Su

doi:10.1021/jo500576x

Cited by 24 publications

(19 citation statements)

References 58 publications

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“…[105] The same group subjected dibenzyl or dialkyl ethers 195 as an acylating source for the acylation of 2-acyl phenols 198 and 1,3dicarbonyl compounds 199 via Cu-catalyst in the presence of TBHP (Scheme 50b). [106] In 2016, Phan group applied Cu 2 (dhtp) cheap acylation reagents in synthesis of the aromatic ketones 209 by Pd-catalysed regioselective ortho-acylation of 2-arylpyridine 6 in the presence of TBHP. Further, the mechanistic study shows that the reaction of 2-phenylpyridine 6 with PdCl 2 forms palladacycle, which then reacts with acyl radical (from oxidation of benzylamine by TBHP) leads to ortho-acylation products 209 (Scheme 54).…”

Section: Ethersmentioning

confidence: 99%

Alternative and Uncommon Acylating Agents – An Alive and Kicking Methodology

Sivaraj

Gandhi

2021

Chemistry An Asian Journal

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Functionalizing and derivatising organic molecules is a centerpiece in organic synthesis. Succinctly manipulating and installing acyl moieties in organic molecules spurred the interest of chemists owing to its occurrence in natural products, bioactive molecules, pharmaceuticals, and advanced materials. Traditionally, access to acylation reaction was achieved by Friedel-Crafts reaction, Schotten-Baumann, and Vilsmeier-Haack acylation, however, these protocols own pitfalls. Further to make the acylation process attractive and environmentally friendly, toluene, aldehydes, alcohols, α-keto acids, amines, amides, esters, ethers, nitriles, alkynes, alkenes, ketenes, N-acylbenzotriazoles, ketones, thioacids, oximes, thiazolium carbinols, PIDA, diacyl disulfides and acyl salts were used as an acyl surrogates/reagents. Amusingly, these acylating reagents are considered uncommon and alternative to carboxylic acids, acid chlorides and acetic anhydrides. This short review aims to encompass the usage of acylating agents in transition-metal, metal-free, light-driven and other demanding conditions, and thus reveals their practicality.

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Section: Ethersmentioning

confidence: 99%

Alternative and Uncommon Acylating Agents – An Alive and Kicking Methodology

Sivaraj

Gandhi

2021

Chemistry An Asian Journal

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“…A metal‐free tetrabutylammonium iodide (TBAI)‐based catalytic system has recently been developed; further atom‐economical mild condensation of ketones with benzylic alcohols in the presence of TBHP ( tert ‐butyl hydroperoxide) gives α‐acyloxycarbonyl compounds (Scheme ). Another related protocol (Scheme ) provides phenol and enol esters in good yields with high chemoselectivity …”

Section: Overview Of Recent Advances In Chemospecific One‐pot Transfmentioning

confidence: 99%

Recent Advances in Cascade Reactions Initiated by Alcohol Oxidation

2016

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In this review, we attempt to answer the question: how can we construct complex functionalized molecules with significant added value from cheap and readily available alcohols in the simplest and most efficient manner? Accordingly, recent developments (mainly from the last five years) in the field of one‐pot multiple transformations of alcohols are overviewed in terms of process simplification and optimization; sustainability; and atom, bond, step, and redox economy. Particular attention is paid to chemo‐ and stereoselective transformations with specific formation of particular bonds and configurations, leaving other parts of substrates unchanged.

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“…Ethers 338 were subjected to oxidative coupling with 1,3-dicarbonyl compounds 339 and o -acylphenols 340 using the copper salt/ t- BuOOH system to prepare esters 341 and 342 ( Scheme 77 ) [ 275 ].…”

Section: Reviewmentioning

confidence: 99%

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

Krylov

Vil

Terent’ev

2015

Beilstein J. Org. Chem.

171

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SummaryThe present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond, is called the CH-reagent or the C-reagent, and the compound, an oxygen atom of which is involved in the new bond, is called the OH-reagent or the O-reagent. Alcohols and carboxylic acids are most commonly used as O-reagents; hydroxylamine derivatives, hydroperoxides, and sulfonic acids are employed less often. The cross-dehydrogenative C–O coupling reactions are carried out using different C-reagents, such as compounds containing directing functional groups (amide, heteroaromatic, oxime, and so on) and compounds with activated C–H bonds (aldehydes, alcohols, ketones, ethers, amines, amides, compounds containing the benzyl, allyl, or propargyl moiety). An analysis of the published data showed that the principles at the basis of a particular cross-dehydrogenative C–O coupling reaction are dictated mainly by the nature of the C-reagent. Hence, in the present review the data are classified according to the structures of C-reagents, and, in the second place, according to the type of oxidative systems. Besides the typical cross-dehydrogenative coupling reactions of CH- and OH-reagents, closely related C–H activation processes involving intermolecular C–O bond formation are discussed: acyloxylation reactions with ArI(O2CR)2 reagents and generation of O-reagents in situ from C-reagents (methylarenes, aldehydes, etc.).

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Copper-Catalyzed Oxidative C–O Bond Formation of 2-Acyl Phenols and 1,3-Dicarbonyl Compounds with Ethers: Direct Access to Phenol Esters and Enol Esters

Cited by 24 publications

References 58 publications

Alternative and Uncommon Acylating Agents – An Alive and Kicking Methodology

Alternative and Uncommon Acylating Agents – An Alive and Kicking Methodology

Recent Advances in Cascade Reactions Initiated by Alcohol Oxidation

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

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