An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C–H Bond

Liu, Saiwen; Chen, Ru; He, Guoqiu; Zhang, Jin

doi:10.3390/molecules25071527

Cited by 4 publications

(1 citation statement)

References 29 publications

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“…Liu and Zhang with coworkers also studied benzylic C(sp 3 )‐H acyloxylation of diarylmethanes. [ 124 ] In contrast to the above contribution by Shen, [ 123 ] only DDQ was used as oxidant in approximately stoichiometric quantities without any cocatalyst and without molecular oxygen. The scope of carboxylic acid was significantly expanded compared to Pan et al, [ 123 ] and good to high yields (62–93 %, Scheme 32) of acyloxylated products were documented.…”

Section: Metal‐free Acyloxylationsmentioning

confidence: 99%

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Antonov

Bryliakov

2022

Applied Organom Chemis

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Herewith, recent progress in the transition metal catalyzed, as well as metal‐free and electrochemical selective acyloxylations of C(sp3)‐H bonds is surveyed. The corresponding modifications of different substrate types such as amines, amides, oximes, aminoacids, nitrogen‐containing heterocycles, olefins, carbonyl compounds, carboxylic acids, and acetals are covered, focusing on their synthetic potential. Correlations between the nature of the catalyst, oxidant, additives, conditions, and the acyloxylation regio‐ and chemoselectivity, are revealed, and available mechanistic details are discussed briefly. The time span of the review is 2015 to present time.

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Section: Metal‐free Acyloxylationsmentioning

confidence: 99%

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Antonov

Bryliakov

2022

Applied Organom Chemis

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Metal‐Free Oxidative CH Bond Functionalization

Dahatonde¹,

Bisht²,

Batra³

2022

Handbook of CH-Functionalization

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Direct replacement of an inert CH bond with a functional group is traditionally termed CH bond functionalization. Remarkable progress in the strategies for CH functionalization has enabled organic chemists to take advantage of the ubiquity of the CH bond in the chemical feedstock to construct complex molecules. The CH bond functionalizations, resulting in a CC or C–hetero bond that is conventionally achieved via metal‐mediated activation of inert CH bond, are now of paramount importance in modern synthetic chemistry. However, growing environmental concerns and issues about sustainability have inspired the development of metal‐free approaches to such useful CH functionalization reactions under oxidative conditions. During the last decade, there has been profound progress in the development of a variety of innovative metal‐free oxidative CH functionalization reactions and this article presents the assimilation of the literature since 2015, concerning the construction of CC and C–hetero (N, O, S, Se, Te, P, B) bonds using the strategy.

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Photoredox/Copper Dual-Catalyzed Benzylic C–H Esterification via Radical-Polar Crossover

et al. 2022

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Herein, we report a distinctive photoredox/copper dual-catalyzed esterification of benzylic C–H bonds through the combination of photoredox-mediated hydrogen atom transfer and Cu(II)-mediated radical-polar crossover. This methodology demonstrates a high functional group tolerance (>40 examples) and moderate to good yields with structurally diverse benzylic C–H substrates. Notably, stoichiometric amounts of carboxylic acids are used as coupling partners, which allows the synthesis of structurally diverse benzylic esters and the late-stage functionalization of pharmaceuticals.

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An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C–H Bond

Cited by 4 publications

References 29 publications

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Metal‐Free Oxidative CH Bond Functionalization

Photoredox/Copper Dual-Catalyzed Benzylic C–H Esterification via Radical-Polar Crossover

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An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C–H Bond

Cited by 4 publications

References 29 publications

Recent progress in catalytic acyloxylation of C(sp3)‐H bonds

Recent progress in catalytic acyloxylation of C(sp3)‐H bonds

Metal‐Free Oxidative CH Bond Functionalization

Photoredox/Copper Dual-Catalyzed Benzylic C–H Esterification via Radical-Polar Crossover

Contact Info

Product

Resources

About

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds

Recent progress in catalytic acyloxylation of C(sp³)‐H bonds