Palladium-Catalyzed Direct Ortho Aroylation of 2-Phenoxypyridines with Aldehydes and Catalytic Mechanism Investigation

Chu, Jean‐Ho; Chen, Shih-Tien; Chiang, M; Wu, Ming‐Jung

doi:10.1021/om501330h

Cited by 51 publications

(22 citation statements)

References 68 publications

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“…22 In this report, detailed mechanistic experiments were conducted including intra- and intermolecular kinetic isotope effects, radical trapping, and controlled experiments. The authors proposed a Pd(III) or Pd(IV) π -complex as a key intermediate along the catalytic cycle and a reaction pathway that proceeds via conversion of the aldehyde to an acyl radical.…”

Section: Aldehydesmentioning

confidence: 99%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

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The transition metal-catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds has emerged as a particularly efficient and powerful approach for the construction of an incredibly diverse array of heteroatom substituted products. Readily available and stable inputs are typically employed, and reactions often proceed with very high functionality group compatibility and without the production of waste byproducts. Additionally, many transition metal-catalyzed C–H bond additions to polarized π-bonds occur within cascade reaction sequences to provide rapid access to a diverse array of different heterocyclic as well as carbocyclic products. This review highlights the diversity of transformations that have been achieved, catalysts that have been used, and types of products that have been prepared through the transition metal catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds.

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Section: Aldehydesmentioning

confidence: 99%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

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“…More recently, Wu and co‐workers reported their study on the ortho ‐aroylation of 2‐phenoxypyridines with aldehydes 19. By using palladium(II) acetate, tert ‐butyl hydroperoxide, and chlorobenzene as the catalytic system, aryl ketones were formed generally in good yields (Scheme ).…”

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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“…Wu and co-workers reported that the ortho-aroylation of 2phenoxypyridines with aldehydes could proceed efficientlyi n the presenceo ftert-butyl hydroperoxide (TBHP;S cheme 9). [13] The reactions produced mixture of mono-aroylateda nd di-aroylated phenol derivatives. However, these two products could be easily separated.…”

Section: Acylationmentioning

confidence: 99%

Transition Metal‐Catalyzed Directing‐Group‐Assisted C−H Activation of Phenols

Luo

2019

ChemSusChem

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Strategies that exploit directing groups to control the site selectivity in the C−H activation of arenes have received much attention during the past two decades. In light of the importance of phenol derivatives in the areas of pharmaceuticals, agrochemicals, and materials science, transition‐metal‐catalyzed C−H activation of phenols has proven to be an extremely useful tool in organic synthesis. This Minireview summarizes the current state‐of‐the‐art direct C−H activation of phenol derivatives under transition‐metal catalysis.

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Palladium-Catalyzed Direct Ortho Aroylation of 2-Phenoxypyridines with Aldehydes and Catalytic Mechanism Investigation

Cited by 51 publications

References 68 publications

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

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

Transition Metal‐Catalyzed Directing‐Group‐Assisted C−H Activation of Phenols

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