Unified Strategy to Access 6H‐Benzofuro[2,3‐b]indoles and 5,6‐Dihydroindolo[2,3‐b]indoles via UV Light‐Mediated Diradical Cyclization

Cheng, Bin; Zu, Bing; Li, Yuntong; Zhai, Shengxian; Xu, Wei; Li, Yun; Zhai, Hongbin

doi:10.1002/adsc.201701270

Cited by 13 publications

(8 citation statements)

References 36 publications

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“…(Scheme 27). [22] The authors found that the diradical cyclization efficiently took place when a 250 W high‐pressure Hg UV‐365 lamp was used for irradiation in THF medium with a 6 mM concentration of the reactant. The method could also afford 6 H ‐benzofuro[2,3‐ b ]indoles in addition to the indolo[2,3‐ b ]indoles mentioned in Scheme 27.…”

Section: Methods For the Synthesis Of Indolo[23‐b]indolesmentioning

confidence: 99%

“…While a recurring theme in the synthetic methods has been to employ derivatives of indoles as the starting substrates, [12a,13] authors have also obtained indoloindoles starting from anilines, [5d,14] arynes, [15] or naphthalene derivatives [16] . Indoloindoles may not only be accessed by employing metals such as Cu, [15] Ru, [17] Rh, [18] Pd, [19] or Au, [20] but also in metal‐free aerobic conditions [21] as well as under the influence of UV‐irradiation [22] . There are also methods reported to access densely functionalized indoloindoles in catalyst‐free mechanochemical conditions, [23] thereby highlighting recent synthetic methods’ immense diversity and versatility.…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances towards the Synthesis and Material Applications of Indoloindoles

Paul

John

2022

Chemistry An Asian Journal

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An important class of N-heteroacenes is indoloindoles which are air-stable, electron-rich and possess many tuneable properties. Initially, indoloindoles were explored for potential biological applications but current interest is based on their performance as photovoltaic materials. With growing applications of indoloindoles across multiple facets as organic functional materials, the need for efficient methods to synthesize and functionalize indoloindoles has taken a centre stage. Over the years, synthetic routes leading to indoloindoles have evolved from multistep protocols to one-pot multicomponent synthesis. Present literature boasts of a variety of reports that employ metals such as Cu, Ru, Rh, Pd, or Au to mediate the reaction towards indoloindoles. As alternatives to such metal-mediated methods, researchers have also developed metal-free and catalyst-free conditions. Indoloindoles, which are fundamentally fused-indoles, are often synthesized by transforming indole derivatives but methods that employ anilines or arynes as the starting substrates are equally abundant. The present review highlights the rich diversity and versatility of recent literature for the synthesis of indolo[3,2-b]indoles, indolo[2,3-b]indoles, indolo[7,6-g]indoles, and indolo [5,4-e]indoles. This review discusses protocols that were explicitly designed to obtain the above-mentioned indoloindoles and also explores several other methods that can be adapted to access said heteroacenes. Available mechanistic details pertaining to novel transformations have been detailed for the readers. Various applications where indoloindoles function as organic lightemitting diodes, organic field-effect transistors, solar cells, etc. have also been delved into before concluding with an outlook on future research.

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Section: Methods For the Synthesis Of Indolo[23‐b]indolesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Advances towards the Synthesis and Material Applications of Indoloindoles

Paul

John

2022

Chemistry An Asian Journal

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“…Consequently, the chemistry of the furoindolines has witnessed an explosive resurgence because of the availability of a concise method for their preparation mediated by metal complexes such as Fe, Ag, Pd, and Cu . Furthermore, metal-free conditions have also been developed, including NIS-, hypervalent iodine(III)-, electrochemical-, and Bronsted acid-, Lewis acid-, radical-, and organocatalyst-promoted transformations.…”

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confidence: 99%

Revisiting Furodiindolines: One-Pot Synthesis of Furodiindolines Using Indole 2,3-Epoxide Surrogates and Their Synthetic Applications

et al. 2019

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Furodiindolines have emerged as versatile intermediates in various transformations, which are easily obtained from indole 2,3-epoxide surrogates via a one-pot procedure and allowed access to heterocyclic compounds with structural diversity and complexity. Four types of transformations from the furodiindolines have been achieved: (i) dehydrative rearrangement to afford 2,3′biindoles, (ii) hydrolysis/cyclization to give 3,4-disubstituted quinolines, (iii) ring-opening/cyclization to give pyrroloindolines, and (iv) aminal cleavage to give a 3,3-disubstituted 2-oxindole.

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“…In the past decades, though oxygenation reactions with molecular oxygen catalyzed by transition metals have been significantly explored, synthesis of oxygen-containing compounds via the directing-group-assisted C–H bond functionalization cascade approaches remain rather rare. As part of our continuing efforts on the cobalt-catalyzed C(sp 2 )–H bond functionalization reaction assisted by the 2-(1′-methylhydrazinyl)pyridine (MHP), which is an advantageous bidentate directing group because of its inexpensive access and convenient removal, development of novel synthetic methods for the efficient construction of heterocyclic compounds has been vigorously pursued . We report herein for the first time a unique approach for cobalt-catalyzed trifunctionalization of allenes to afford a series of versatile 3-acylquinoline derivatives.…”

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confidence: 99%

Trifunctionalization of Allenes via Cobalt-Catalyzed MHP-Assisted C–H Bond Functionalization and Molecular Oxygen Activation

et al. 2018

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We have developed an approach for the cobalt-catalyzed trifunctionalization of allenes to form versatile 3-acylquinolines in the presence of molecular oxygen with moderate to good yields in high regioselectivity. C–H bond functionalization of benzoic hydrazides assisted by the 2-(1′-methylhydrazinyl)pyridine (MHP) acted as a key step in the cascade reaction. The reaction shows broad functional group tolerance of both allenes and hydrazides. Moreover, relevant experiments have been performed to probe the reaction mechanism.

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Unified Strategy to Access 6H‐Benzofuro[2,3‐b]indoles and 5,6‐Dihydroindolo[2,3‐b]indoles via UV Light‐Mediated Diradical Cyclization

Cited by 13 publications

References 36 publications

Recent Advances towards the Synthesis and Material Applications of Indoloindoles

Recent Advances towards the Synthesis and Material Applications of Indoloindoles

Revisiting Furodiindolines: One-Pot Synthesis of Furodiindolines Using Indole 2,3-Epoxide Surrogates and Their Synthetic Applications

Trifunctionalization of Allenes via Cobalt-Catalyzed MHP-Assisted C–H Bond Functionalization and Molecular Oxygen Activation

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