Palladium‐Catalyzed Regioselective Acylation of Diazines with Toluenes: A New Approach to the Synthesis of <i>ortho</i>‐Diacylbenzenes

Kianmehr, Ebrahim; Seifinoferest, Behnoush; Afaridoun, Hadi

doi:10.1002/ejoc.202000364

Cited by 4 publications

(2 citation statements)

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“…of TBHP as an oxidant at 140 °C in chlorobenzene (Scheme 28). [43] However, further improvement in yield was not observed even after increasing the catalyst loading. It was noticed that lowering the reaction temperature decreased the reaction yield under this catalytic conditions.…”

Section: C(sp2)‐h Acylation Of Diazinesmentioning

confidence: 99%

Pd(II)‐Catalyzed Chelation‐Induced C(sp²)‐H Acylation of (Hetero)Arenes Using Toluenes as Aroyl Surrogate

et al. 2021

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In the last few years, transition‐metal‐catalyzed chelation‐controlled ortho‐acylation utilizing methyl arene as the acyl partner has emerged as a powerful technique to achieve diverse complexity with diaryl ketone skeleton contrast to the traditional cross‐coupling/Friedel‐Craft reaction. Diaryl ketones are a significant building block that exists in pharmaceuticals, agrochemicals, natural products, functional materials, and many other useful compounds. In this context, the up‐to‐date developments in Pd(II)‐catalyzed ortho‐acylations of arenes and heteroarenes with toluenes as acyl surrogate are studied with advantages, limitations, mechanistic pathways, and prospective.

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Section: C(sp2)‐h Acylation Of Diazinesmentioning

confidence: 99%

Pd(II)‐Catalyzed Chelation‐Induced C(sp²)‐H Acylation of (Hetero)Arenes Using Toluenes as Aroyl Surrogate

et al. 2021

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“…Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions are well-known and frequently used methods to form C-C and C-heteroatom bonds via Pd(II)/Pd(0), Pd(II)/Pd(IV), Pd(0)/ Pd(II)/Pd(IV), and Pd(0)/Pd(II) catalytic cycles, 51,52 namely in some previously reported methods by the current research group. 53,54 Palladium-assisted methods have also been frequently used for the synthesis of coumarin derivatives.…”

Section: Palladiummentioning

confidence: 99%

Modern metal-catalyzed and organocatalytic methods for synthesis of coumarin derivatives: a review

Farid¹,

Seifinoferest²,

Gholamhosseyni³

et al. 2022

Org. Biomol. Chem.

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Rhodium-Catalyzed Azine-Directed C–H Amidation with N-Methoxyamides

Ban

Zhang

et al. 2022

J. Org. Chem.

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Using N-methoxyamide reagents as an amide source, C–H amidation was realized at the ortho position of azine under the action of rhodium and boric acid. The method has mild reaction conditions, high atomic utilization, excellent yield, and wide adaptability to amidation reagents (both aromatic amides and fatty amides are applicable). Amide-substituted ketones can be obtained by a simple treatment and can be further transformed into bioactive substances. This provides a good supplement for the C–H bond amidation of aromatic rings.

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Palladium‐Catalyzed Regioselective Acylation of Diazines with Toluenes: A New Approach to the Synthesis of ortho‐Diacylbenzenes

Abstract: A highly efficient and practical procedure for chemoand regioselective synthesis of ortho-diacylbenzenes through Pd-catalyzed oxidative C-H bond activation has been developed. Using this method, a variety of ortho-diacylbenzenes

Cited by 4 publications

References 35 publications

Pd(II)‐Catalyzed Chelation‐Induced C(sp²)‐H Acylation of (Hetero)Arenes Using Toluenes as Aroyl Surrogate

Pd(II)‐Catalyzed Chelation‐Induced C(sp²)‐H Acylation of (Hetero)Arenes Using Toluenes as Aroyl Surrogate

Modern metal-catalyzed and organocatalytic methods for synthesis of coumarin derivatives: a review

Rhodium-Catalyzed Azine-Directed C–H Amidation with N-Methoxyamides

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Palladium‐Catalyzed Regioselective Acylation of Diazines with Toluenes: A New Approach to the Synthesis of ortho‐Diacylbenzenes

Abstract: A highly efficient and practical procedure for chemoand regioselective synthesis of ortho-diacylbenzenes through Pd-catalyzed oxidative C-H bond activation has been developed. Using this method, a variety of ortho-diacylbenzenes

Cited by 4 publications

References 35 publications

Pd(II)‐Catalyzed Chelation‐Induced C(sp2)‐H Acylation of (Hetero)Arenes Using Toluenes as Aroyl Surrogate

Pd(II)‐Catalyzed Chelation‐Induced C(sp2)‐H Acylation of (Hetero)Arenes Using Toluenes as Aroyl Surrogate

Modern metal-catalyzed and organocatalytic methods for synthesis of coumarin derivatives: a review

Rhodium-Catalyzed Azine-Directed C–H Amidation with N-Methoxyamides

Contact Info

Product

Resources

About

Pd(II)‐Catalyzed Chelation‐Induced C(sp²)‐H Acylation of (Hetero)Arenes Using Toluenes as Aroyl Surrogate

Pd(II)‐Catalyzed Chelation‐Induced C(sp²)‐H Acylation of (Hetero)Arenes Using Toluenes as Aroyl Surrogate