Pd‐Catalyzed C(sp
            <sup>3</sup>
            )H Activation by Native Directing Groups

Babu, Srinivasarao Arulananda; Padmavathi, Rayavarapu; Aggarwal, Yashika; Kaur, Ramandeep; Suwasia, Sonam

doi:10.1002/9783527834242.chf0006

Cited by 3 publications

(1 citation statement)

References 248 publications

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“…Subsequently, we intended to explore the native carboxylic acid group aided C–H arylation 2p q of carbazole-3-carboxylic acid 4a (Table 2 ). Towards this end, we performed the β-C–H arylation of N -ethylcarbazole-3-carboxylic acid ( 4a ) with 6a in the presence of Pd(OAc) 2 as catalyst (6–10 mol%) and NMe 4 Cl and KOAc as additives in AcOH or TFA at 120 °C for 24 hours.…”

Section: Table 1 Screening Of Reaction Conditions For T...mentioning

confidence: 99%

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation, Alkylation, Benzylation, and Methoxylation of Carbazole-3-carboxamides toward C2,C3,C4-Functionalized Carbazoles

2023

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We report the Pd(II)-catalyzed, bidentate directing group 8-aminoquinoline or 2-(methylthio)aniline-assisted β-C-H arylation, alkylation, benzylation and methoxylation of carbazole-3-carboxamide, carbazole-2-carboxamide substrates and construction of C2,C3,C4 functionalized carbazole motifs. The Pd(II)-catalyzed β-C-H arylation reaction was attempted using different directing groups such as 8-aminoquinoline, 2-(methylthio)aniline, 4-amino-2,1,3-benzothiadiazole, 4-methoxyquinolin-8-amine and butan-1-amine. Through optimization of reactions, the 8-aminoquinoline and 2-(methylthio)aniline were found to be suitable directing groups and especially, 2-(methylthio)aniline was found to be an efficient directing group in the Pd(II)-catalyzed β-C-H arylation, alkylation, methoxylation of carbazole-3-carboxamide, carbazole-2-carboxamide substrates. An ample number of β-C-H arylated, alkylated, benzylated and methoxylated carbazole-3-carboxamides were synthesized. The structures of representative β-C(2)-H arylated carbazole and β-C(2)-H methoxylated carbazole motifs were unequivocally confirmed by the single-crystal X-ray structure analysis. Given the wide range of applications of carbazoles in chemical, materials sciences and medicinal chemistry and there have been constant efforts for developing new methods and synthesizing functionalized carbazoles. This work contributes to the expansion of the library of the C2,C3,C4 functionalized carbazole motifs through the Pd(II)-catalyzed directing group-aided site-selective β-C-H activation and functionalization of carbazole-3-carboxamides.

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Section: Table 1 Screening Of Reaction Conditions For T...mentioning

confidence: 99%

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation, Alkylation, Benzylation, and Methoxylation of Carbazole-3-carboxamides toward C2,C3,C4-Functionalized Carbazoles

2023

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Cu-Catalyzed Oxidative C(sp²)–H Cycloetherification of o-Alkenyl Arenols for the Preparation of Fused Furans

Yaragorla,

Khan,

Raoof

2023

J. Org. Chem.

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A practically efficient, copper-catalyzed approach for the synthesis of functionally embellished indeno-naphthofurans is developed from 1-(1H-inden-3-yl)naphthalen-2-ols. This intramolecular cycloetherification proceeds via C(sp 2 )−H oxygenation (C−H bond breaking and C−O bond forming), which enables the atom-economical synthesis of poly fused furans in high yields with large substrate diversity in the open air.

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Palladium-Catalyzed Annulations via Sequential C–H Activations of C(sp²)–H/C(sp³)–H or C(sp³)–H/C(sp³)–H Bonds

Wei,

Czajkowski,

Kuang

et al. 2024

ACS Catal.

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Palladium-catalyzed C−H annulation reactions represent a compelling strategy to construct complex ring systems with high step economy. While there are many approaches to annulate structures by activation of a single C−H bond, transformations that proceed by activation of multiple C−H bonds are less explored. This is especially true for examples where one of the reacting C−H bonds is located at an sp 3 center. However, exciting developments in palladium-catalyzed C−H activation continue to expand the scope of these transformations and provide innovative strategies to construct challenging carbon− carbon bonds. From these discoveries, sequential C−H activations have emerged as a powerful tool to access complex ring systems through the activation of C(sp 2 )−H/C(sp 3 )−H or C(sp 3 )−H/C(sp 3 )−H bonds. In this Perspective, we showcase recent examples that use this strategy in order to highlight the synthetic potential of C−H activation-enabled annulations and inspire future use of these disconnections for diverse scaffold synthesis.

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Pd‐Catalyzed C(sp ³ )H Activation by Native Directing Groups

Cited by 3 publications

References 248 publications

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation, Alkylation, Benzylation, and Methoxylation of Carbazole-3-carboxamides toward C2,C3,C4-Functionalized Carbazoles

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation, Alkylation, Benzylation, and Methoxylation of Carbazole-3-carboxamides toward C2,C3,C4-Functionalized Carbazoles

Cu-Catalyzed Oxidative C(sp²)–H Cycloetherification of o-Alkenyl Arenols for the Preparation of Fused Furans

Palladium-Catalyzed Annulations via Sequential C–H Activations of C(sp²)–H/C(sp³)–H or C(sp³)–H/C(sp³)–H Bonds

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Pd‐Catalyzed C(sp 3 )H Activation by Native Directing Groups

Cited by 3 publications

References 248 publications

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation, Alkylation, Benzylation, and Methoxylation of Carbazole-3-carboxamides toward C2,C3,C4-Functionalized Carbazoles

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation, Alkylation, Benzylation, and Methoxylation of Carbazole-3-carboxamides toward C2,C3,C4-Functionalized Carbazoles

Cu-Catalyzed Oxidative C(sp2)–H Cycloetherification of o-Alkenyl Arenols for the Preparation of Fused Furans

Palladium-Catalyzed Annulations via Sequential C–H Activations of C(sp2)–H/C(sp3)–H or C(sp3)–H/C(sp3)–H Bonds

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Product

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Pd‐Catalyzed C(sp ³ )H Activation by Native Directing Groups

Cu-Catalyzed Oxidative C(sp²)–H Cycloetherification of o-Alkenyl Arenols for the Preparation of Fused Furans

Palladium-Catalyzed Annulations via Sequential C–H Activations of C(sp²)–H/C(sp³)–H or C(sp³)–H/C(sp³)–H Bonds