Visible-Light-Mediated Ir(III)-Catalyzed Concomitant C3 Oxidation and C2 Amination of Indoles

Shukla, Geeta; Alam, Tipu; Srivastava, H. K.; Kumar, Ritush; Patel, Bhisma K.

doi:10.1021/acs.orglett.9b00887

Cited by 23 publications

(9 citation statements)

References 55 publications

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“…While Borhan et al described C3-oxidation and C2-amination of C2-occupied indoles with hydroxycar- bamate as the amination reagent under copper catalysis (Scheme 62, a), [139] Patel and co-workers accomplished a concomitant bis-functionalization of indoles under aerobic photocatalysis using arylhydrazides as the coupling partner (Scheme 62, b). [140] A plausible synergistic mechanism for the difunctionalization of indoles is supported by DFT-calculated energy profile.…”

Section: Indole Oxygenationmentioning

confidence: 85%

Aerobic Oxidative Functionalization of Indoles

et al. 2020

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The synthetic methodology for direct indole functionalizations is of great significance in indole chemistry and has been intensively investigated in the last few decades. From the perspective of green chemistry, oxygen is the best choice as the terminal oxidant in molecular synthesis. Hence, aerobic oxidative functionalization of indoles became a hot research topic in the last decade. Numerous efficient protocols in this field have been discovered that enable facile and efficient transformations of indoles to related valuable compounds, which are summarized and discussed in detail in this review.

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Section: Indole Oxygenationmentioning

confidence: 85%

Aerobic Oxidative Functionalization of Indoles

et al. 2020

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“…Patel and co‐workers explored a mild and efficient photocatalytic regioselective strategy for selective difunctionalization of indoles from indoles and benzohydrazides through Ir(III) catalyzed visible‐light‐induced transformations (Scheme 51). [82] A variety of indoles and benzohydrazides can participate in this reactions effectively to provide structurally diverse of oxyindoles in high yields. A feasible mechanism is proposed based on the control experiments and the results of DFT calculations.…”

Section: Photo‐catalyzed/promoted Functionalization Of Indole Derivatmentioning

confidence: 99%

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

2020

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The use of clean and renewable light sources is increasingly common in organic synthesis due to its safety, practicality and economy. Recently, photoredox catalysis has shown great application values in organic transformations because of its advantages of environmentally friendly and abundant resources. Indoles and their derivatives (indolines, oxindoles and isatins) are the core skeletons of some important organic compounds and widely‐present in various natural products and pharmaceuticals with different biological activities. Therefore, the research on the synthesis and modification of indoles is particularly important for chemists and pharmacologists. This review summarizes the effects of photocatalysis on indole synthesis and modification in recent decades. These transformations are accomplished by using metal photocatalysts (i. e., Ir, Ru, Ni, Cu, Fe, Au, Rh, TiO2, etc.) or non‐metallic photocatalysts (i. e., Rose Bengal, Eosin Y, quinones, naphthols, N‐heterocyclic carbenes, carbazoles, pyrylium salts, etc.), or without the need of photocatalysts. The detailed mechanisms of these photo‐catalyzed/promoted organic reactions are also highlighted deeply. And we hope this review will be helpful to researchers interested in this promising field of photocatalyzed transformations.

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“…The reaction proceeds via the attack of singlet oxygen at the C3 position of an indole, followed by amination at the C2 position with benzohydrazides to give difunctionalized indoles (Scheme 84). 87…”

Section: Review Synthesismentioning

confidence: 99%

Recent Advances in Photocatalytic C–N Bond Coupling Reactions

Chan

Chow

2020

Synthesis

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Catalytic C–N bond formation is one of the major research topics in synthetic chemistry owing to the ubiquity of amino groups in natural products, synthetic intermediates and pharmaceutical agents. In parallel with well-established metal-catalyzed C–N bond coupling protocols, photocatalytic reactions have recently emerged as efficient and selective alternatives for the construction of C–N bonds. In this review, the progress made on photocatalytic C–N bond coupling reactions between 2012 and February 2020 is summarized.1 Introduction1.1 General Mechanisms for Photoredox Catalysis1.2 Pioneering Work2 C(sp2)–N Bond Formation2.1 Protocols Involving an External Oxidant2.2 Oxidant-Free Protocols3 C(sp3)–N Bond Formation3.1 Direct Radical–Radical Coupling3.2 Addition Reactions to Alkenes3.3 Reductive Amination of Carbonyl Compounds3.4 Decarboxylative Amination4 Cyclization Reactions4.1 C(sp2)–N Heterocycle Formation4.2 C(sp3)–N Heterocycle Formation5 Other Examples6 Conclusion and Outlook

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Visible-Light-Mediated Ir(III)-Catalyzed Concomitant C3 Oxidation and C2 Amination of Indoles

Cited by 23 publications

References 55 publications

Aerobic Oxidative Functionalization of Indoles

Aerobic Oxidative Functionalization of Indoles

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

Recent Advances in Photocatalytic C–N Bond Coupling Reactions

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