Palladium-catalyzed direct ortho-acylation through an oxidative coupling of 2-arylbenzothiazoles with benzylic alcohols

Ding, Qiuping; Ji, Huafang; Ye, Changqing; Wang, Jiajia; Wang, Junyan; Zhou, Liyun; Peng, Yiyuan

doi:10.1016/j.tet.2013.08.005

Cited by 29 publications

(5 citation statements)

References 45 publications

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“…Under similar reaction conditions, Ding et al. obtained improved yields of the desired products by addition of 1,4‐benzoquinone (BQ; 10 mol %) as an additive (Scheme ) 34b…”

Section: Discussionmentioning

confidence: 99%

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

2015

Chemistry A European J

133

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In this Minireview, the major achievements in the acylation of arenes and heteroarenes by C-H activation with aroyl groups are summarized and discussed. As the products are carbonyl-containing compounds that are typical products from carbonylation chemistry, the possible inspirations for these reactions are also discussed, as are mechanistic issues and possible problems for carbonylative diaryl ketone synthesis by C-H activation.

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“…Under similar reaction conditions, Ding et al. obtained improved yields of the desired products by addition of 1,4‐benzoquinone (BQ; 10 mol %) as an additive (Scheme ) 34b…”

Section: Discussionmentioning

confidence: 99%

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

2015

Chemistry A European J

133

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“…Simultaneously in 2013, Peng and co‐workers [29] employed the same reaction condition introducing benzoquinone (BQ) as the ligand for the stated protocol with 2‐aryl benzothiazole substrates 10 (Condition B, Scheme 8). Substrate exploration studies revealed compatibility with different functionalities except NO 2 containing substrate.…”

Section: C−c Bond Formationmentioning

confidence: 99%

Exploration of C‐H Activation Strategies in Construction of Functionalized 2‐Aryl Benzoazoles: A Decisive Review

2021

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Transition metal‐catalyzed C−H bond activation has proved to be a powerful weapon for the synthesis and functionalization of privileged class of heterocycles. The 2‐aryl benzoazole (benzothiazoles, benzoxazoles and benzimidazoles) derivatives have surfaced in the scientific community with their potential applications in medicinal chemistry, agrochemistry and material science. The contribution of C−H activation strategies towards the functionalization of relevant 2‐aryl benzoazoles has been amenable in the drug discovery process. This review envelopes a decade account of the C−H activation strategies adopted for the functionalization of 2‐aryl benzoazoles.

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“…The highly selective acylation was achieved by the directing group, i. e., a nitrogen unit in arylbenzothiazoles 175 (Scheme 43d). [90] In 2014, Zeng et al used alcohol 169 as an acylating agent for ortho-acylation of azoarenes 66 via Pd-catalyst in the presence of TBHP as an oxidant. This cascade oxidative CÀ H crosscoupling was assisted by azo directing group to achieve acylation at ortho-position (Scheme 43e).…”

Section: Alcoholsmentioning

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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Palladium-catalyzed direct ortho-acylation through an oxidative coupling of 2-arylbenzothiazoles with benzylic alcohols

Cited by 29 publications

References 45 publications

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

Exploration of C‐H Activation Strategies in Construction of Functionalized 2‐Aryl Benzoazoles: A Decisive Review

Alternative and Uncommon Acylating Agents – An Alive and Kicking Methodology

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