Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

Yuan, Yu‐Chao; Bruneau, Christian; Dorcet, Vincent; Roisnel, Thierry; Gramage‐Doria, Rafael

doi:10.1021/acs.joc.8b02899

Cited by 29 publications

(12 citation statements)

References 95 publications

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“…Polyaromatic substrates 26-28c were also shown to be highly reactive. As a prominent structural motif, N-arylpyrrolidinones have been used in Ru(II)-catalysed C-H hydroxylation 56,57 . We found that the boron-mediated directed C-H hydroxylation of N-phenylpyrrolidinone (29a) in the presence of BBr 3 could provide the desired product 29c with a 79% yield.…”

Section: Resultsmentioning

confidence: 99%

Boron-mediated directed aromatic C–H hydroxylation

Lv¹,

Zhao²,

Yu³

et al. 2020

Nat Commun

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Transition metal-catalysed C-H hydroxylation is one of the most notable advances in synthetic chemistry during the past few decades and it has been widely employed in the preparation of alcohols and phenols. The site-selective hydroxylation of aromatic C-H bonds under mild conditions, especially in the context of substituted (hetero)arenes with diverse functional groups, remains a challenge. Here, we report a general and mild chelation-assisted C-H hydroxylation of (hetero)arenes mediated by boron species without the use of any transition metals. Diverse (hetero)arenes bearing amide directing groups can be utilized for ortho C-H hydroxylation under mild reaction conditions and with broad functional group compatibility. Additionally, this transition metal-free strategy can be extended to synthesize C7 and C4-hydroxylated indoles. By utilizing the present method, the formal synthesis of several phenol intermediates to bioactive molecules is demonstrated.

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Section: Resultsmentioning

confidence: 99%

Boron-mediated directed aromatic C–H hydroxylation

Lv¹,

Zhao²,

Yu³

et al. 2020

Nat Commun

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“…of (NH 4 ) 2 S 2 O 8 in (3:1) TFA/TFAA at 80 0 C successfully removed the ortho-proton of N-phenyl phthalimides for selective hydroxylation (Scheme 41). [55] The reaction proceeds via the formation of favorable six membered ruthenacycle (activat- Based on their previous work, [30] Singh et. al.…”

Section: Tfa Mediated Hydroxylationmentioning

confidence: 99%

“…of (NH 4 ) 2 S 2 O 8 in (3:1) TFA/TFAA at 80 0 C successfully removed the ortho ‐proton of N ‐phenyl phthalimides for selective hydroxylation (Scheme 41). [55] The reaction proceeds via the formation of favorable six membered ruthenacycle (activating H a ) rather than five membered (with H b ) cyclic intermediate for selective hydroxylation of C−H bond. A large number of imides with diverse functional groups like Me, NEt 2 , F, Cl, NO 2 , CO 2 Et etc.…”

Section: Tfa− From Tfa and Phi(otfa)2 As Hydroxylating Agentmentioning

confidence: 99%

Recent Advancements on Transition‐Metal‐Catalyzed, Chelation‐Induced ortho‐Hydroxylation of Arenes

Iqbal

Joshi

2020

Adv Synth Catal

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The phenols are key intermediates as well as desired products in many target oriented syntheses. The conversion of CÀ H bond to CÀ O bond is one of the most challenging tasks in organic synthesis. In last few decades, the hydroxylation of aromatic compounds has drawn a considerable attention because of their importance in Pharmaceutical industry, material chemistry, polymers and in agrochemicals. Indeed, transition-metal-catalyzed, coordination-assisted regio-and chemoselective orthohydroxylation of arenes has become very efficient and popular strategy to obtain good yields of phenols with tolerance of a wide range of functional groups. This review is the comprehensive summary of recent advancement on Pd-, Ru-, Rh-, Cu-and Ir-catalyzed, chelation-controlled regioselective ortho-CÀ H bond hydroxylation of aromatic compounds in the presence of diverse hydroxylating agents. The review has been classified on the sources of hydroxylating agents used in reaction.

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“…Alternatively, N ‐arylphthalimide derivatives were found to be suitable partners to provide exclusively mono‐hydroxylated products with anilide site‐selectivity regardless of the equivalents of oxidant being used (Scheme ) . The reactions, which were catalyzed by ruthenium or palladium catalysts, were tolerant to a broad scope of functional groups.…”

Section: C−o Bond Forming Reactionsmentioning

confidence: 99%

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

Gramage‐Doria

2020

Chemistry A European J

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SelectiveC ÀHb ond functionalization catalyzed by metal complexes have completely revolutionized the wayi n which chemical synthesis is conceived nowadays. Typically, the reactivityo fat ransitionm etal catalyst is the key to control the site-, regio-and/or stereo-selectivity of aC ÀHb ond functionalization. Of particulari nterests are molecules that contain multiple CÀHb onds prone to undergo CÀHb ond activations with very similar bond dissociation energies at different positions. This is the case of benzanilides, relevant chemical motifs that are found in many useful fine chemicals, in which two CÀHs ites are present in chemically different aromatic fragments. In the last years, it has been found that depending on the metal catalyst and the reaction conditions, the amide motif might behave as ad irecting group towardst he metal-catalyzed CÀHb ond activation in the benzamide site or in the anilides ite. The impact and the consequences of such subtle control of site-selectivity are herein reviewed with important applicationsi ncarboncarbon and carbon-heteroatomb ond forming processes. The mechanisms unraveling these unique transformations are discussed in order to provide ab etter understanding for future developmentsi nt he field of site-selective CÀHb ond functionalization with transition metal catalysts.

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Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

Cited by 29 publications

References 95 publications

Boron-mediated directed aromatic C–H hydroxylation

Boron-mediated directed aromatic C–H hydroxylation

Recent Advancements on Transition‐Metal‐Catalyzed, Chelation‐Induced ortho‐Hydroxylation of Arenes

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

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