Palladium‐Catalyzed Oxidative CC Bond Cleavage of α‐Hydroxyketones: Application to CH Acylation of Azoarenes and Synthesis of a Liver(X) Receptor Agonist

Majhi, Biju; Ahammed, Sabir; Kundu, Debasish; Ranu, Brindaban C.

doi:10.1002/ajoc.201402280

Cited by 11 publications

(8 citation statements)

References 87 publications

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“…Additionally, in 2015, α‐hydroxyketones were also explored as aroyl sources and applied in the acylation of azoarenes by Ranu and co‐workers 64. This procedure was applied in the synthesis of a liver receptor agonist.…”

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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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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“…Further, this protocol is entails in synthesis of bioactive molecule, i. e., liver(X) receptor agonist 68 a (Scheme 13). [36]…”

Section: α-Hydroxyketonesmentioning

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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“…It is proposed that the hydroxyketone is oxidized to the corresponding diketone, generating the acyl radical. Both acyl fragments are transferred, so symmetrically substituted 44 have to be used to obtain selective reactions [ 42 ].…”

Section: Acylation Of Arenesmentioning

confidence: 99%

Pd(II)-Catalyzed C-H Acylation of (Hetero)arenes—Recent Advances

2020

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Di(hetero)aryl ketones are important motifs present in natural products, pharmaceuticals or agrochemicals. In recent years, Pd(II)-catalyzed acylation of (hetero)arenes in the presence of an oxidant has emerged as a catalytic alternative to classical acylation methods, reducing the production of toxic metal waste. Different directing groups and acyl sources are being studied for this purpose, although further development is required to face mainly selectivity problems in order to be applied in the synthesis of more complex molecules. Selected recent developments and applications are covered in this review.

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Palladium‐Catalyzed Oxidative CC Bond Cleavage of α‐Hydroxyketones: Application to CH Acylation of Azoarenes and Synthesis of a Liver(X) Receptor Agonist

Cited by 11 publications

References 87 publications

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

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

Alternative and Uncommon Acylating Agents – An Alive and Kicking Methodology

Pd(II)-Catalyzed C-H Acylation of (Hetero)arenes—Recent Advances

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