Ruthenium(II)-catalyzed &lt;I&gt;Ortho&lt;/I&gt; C-O Bond formation of Substituted Aromatics with Oxygen Nucleophiles through C-H Bond Activation

Pimparkar, Sandeep; Padala, Kishor; Jeganmohan, Masilamani

doi:10.16943/ptinsa/2014/v80i5/47969

Cited by 6 publications

(5 citation statements)

References 42 publications

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“…The selective oxidative functionalization of CÀ H bonds is an important process in nature and it is a highly desirable and significant one in chemical industry. Several transition metal catalysts such as Cu, [26] Pd, [27] Ru [28,29] and Fe [30] could mediate CÀ O bond forming processes. The CÀ H bond oxygenation such as hydroxylation, acylation, bezoxylation with ruthenium-catalyst has been developed rapidly in the past few years.…”

Section: Ruthenium-catalysed Cà O Bond Forming Process (Oxygenation)mentioning

confidence: 99%

“…Dias et al [44] described the CÀ H oxygenation of quinone (26) directed by a weakly coordinated oxygen in the presence of ruthenium(II)-catalyst and an oxidant. The catalytic transformation was best performed using [RuCl 2 (p-cymene)] 2 (2 mol%) and the oxidant, PhI(CF 3 CO 2 ) 2 (1.2 eq) in TFAA:TFA (1: 0.02) at 80 °C achieving mono-oxygenated product, juglone (27) in 92 % yield and 3 % of dihyroxylated product (28). On the other hand, the reaction performed with higher catalyst loading (5 mol%) and oxidant (2 eq.)…”

Section: Ruthenium-catalysed Hydroxylationmentioning

confidence: 99%

“…In the past years, the C−H bond functionalization with ruthenium catalysts has been developed rapidly. [1,2 ] Numerous reactions such as C−C, [3] C−N, [4] C−O [5] and C‐halogen [6] bond‐forming processes have been studied with ruthenium‐based catalysts. Murai, Oi and Inoue reported the pioneering work on ruthenium‐catalysed C−H bond alkenylation [7] and arylation [8] .…”

Section: Introductionmentioning

confidence: 99%

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Recent advances in ruthenium‐catalysed aromatic C−H bond oxygenation, nitrogenation and halogenation

Singh

2024

ChemistrySelect

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The transition metal‐catalysed C−H bond functionalization has emerged as a powerful tool for accessing numerous organic compounds in greener manner with step and atom economy. Remarkable progress has been made in the metal‐catalysed C−H bond functionalization during the past decades and the trend is continuing as new reactions are being added. In the transition metal‐catalysed C−H bond functionalization, a growing attention has been paid on ruthenium, particularly, the stable ruthenium(II) as it allows several C−H bond functionalization reactions to perform in water with high selectivity. The ruthenium‐catalysed C−H bond functionalization reactions, such as arylation, alkenylation, annulation, cyanation, amination and silylation just to mention some have been well documented in numerous published papers, book chapters and review articles. However, as ruthenium‐catalysed C−H functionalization has been growing rapidly, a comprehensive review is necessary from time to time to highlight the progress made in this ever expanding field. In view of this, the manuscript presents the ruthenium‐catalysed direct C−O, C−N and C‐halogen bond forming reactions involving aromatic C−H bond covering oxygenation, amination, amidation, imidation, nitration and halogenation reported from 2012 to 2022.

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Section: Ruthenium-catalysed Cà O Bond Forming Process (Oxygenation)mentioning

confidence: 99%

Section: Ruthenium-catalysed Hydroxylationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Recent advances in ruthenium‐catalysed aromatic C−H bond oxygenation, nitrogenation and halogenation

Singh

2024

ChemistrySelect

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“…Generally, the cationic ruthenium species, [RuCl 2 (p-cymene)] 2 /AgSbF 6 or [RuCl 2 (p-cymene)] 2 /KPF 6 have been used for C-H bond functionalization, directed by a weakly coordinatedoxygen and π-bond donor group. The C-H bond functionalization of weakly coordinated directing groups has been extensively studied by the research groups of Jeganmohan [21,22], Ackermann [23] and others [24]. Recently, the benefits of the carboxylic acid ligand in C-H bond functionalization reaction have been explored.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts

Singh

2019

Catalysts

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The past decades have witnessed rapid development in organic synthesis via catalysis, particularly the reactions through C–H bond functionalization. Transition metals such as Pd, Rh and Ru constitute a crucial catalyst in these C–H bond functionalization reactions. This process is highly attractive not only because it saves reaction time and reduces waste,but also, more importantly, it allows the reaction to be performed in a highly region specific manner. Indeed, several organic compounds could be readily accessed via C–H bond functionalization with transition metals. In the recent past, tremendous progress has been made on C–H bond functionalization via ruthenium catalysis, including less expensive but more stable ruthenium(II) catalysts. The ruthenium-catalysed C–H bond functionalization, viz. arylation, alkenylation, annulation, oxygenation, and halogenation involving C–C, C–O, C–N, and C–X bond forming reactions, has been described and presented in numerous reviews. This review discusses the recent development of C–H bond functionalization with various ruthenium-based catalysts. The first section of the review presents arylation reactions covering arylation directed by N–Heteroaryl groups, oxidative arylation, dehydrative arylation and arylation involving decarboxylative and sp3-C–H bond functionalization. Subsequently, the ruthenium-catalysed alkenylation, alkylation, allylation including oxidative alkenylation and meta-selective C–H bond alkylation has been presented. Finally, the oxidative annulation of various arenes with alkynes involving C–H/O–H or C–H/N–H bond cleavage reactions has been discussed.

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“…However, the C–O bond formation has not been well explored. This is most probably due to the high electronegativity of the oxygen element and the strong metal–oxygen bond strength . With the assistance of directing groups, acetoxylation, alkoxylation, hydroxylation, and benzoxylation at the ortho C–H bond of directing group substituted aromatics with various oxygen nucleophiles have been studied.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium-Catalyzed C–H Benzoxylation of tert-Benzamides with Aromatic Acids by Weak Coordination

Padala

Jeganmohan

2017

J. Org. Chem.

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A highly regioselective C-H benzoxylation of tertiary benzamides with aromatic acids by weak O-amide coordination in the presence of [{RuCl(p-cymene)}], AgSbF, and (NH)SO in 1,2-dichloroethane at 100 °C for 24 h to afford ortho-benzoxylated tertiary benzamides is described. Selectively, ortho-benzoxylated cyclic benzamides were converted into ortho-benzoxylated benzaldehydes by using CpZrHCl at room temperature. Subsequently, substituted salicylic acids were prepared by deprotection of the ester and amide groups of ortho-benzoxylated cyclic benzamides.

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Ruthenium(II)-catalyzed <I>Ortho</I> C-O Bond formation of Substituted Aromatics with Oxygen Nucleophiles through C-H Bond Activation

Cited by 6 publications

References 42 publications

Recent advances in ruthenium‐catalysed aromatic C−H bond oxygenation, nitrogenation and halogenation

Recent advances in ruthenium‐catalysed aromatic C−H bond oxygenation, nitrogenation and halogenation

Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts

Ruthenium-Catalyzed C–H Benzoxylation of tert-Benzamides with Aromatic Acids by Weak Coordination

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