Iron-Catalyzed Oxidative Radical Alkoxycarbonylation of Activated Alkenes with Carbazates toward Alkoxycarbonylated Benzimidazo[2,1-a]isoquinolin-6(5H)-ones

Tang, Yucai; Li, Min; Huang, Hongxin; Wang, Feifei; Hu, Xia; Zhang, Xiangyang

doi:10.1055/a-1469-5742

Cited by 11 publications

(2 citation statements)

References 5 publications

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“…Then, the In 2021, Zhang, Tang and co-workers realized a Fe-catalyzed and TBHP-promoted oxidative radical alkoxycarbonylation/cyclization of N-methacryloyl-2-phenylbenzoimidazoles with carbazates (Scheme 82a). [148] One year later, Wu presented a photocatalyzed alkoxycarbonylation/cyclization toward estersubstituted indolo[2,1-a]isoquinolines (Scheme 82b). [149] Alkyloxalyl chlorides that can be easily derived from alcohols and oxalyl chloride were used as alkoxycarbonyl radical sources.…”

Section: Cyclization Of Alkene-tethered 2-arylindoles and 2-aryl Benz...mentioning

confidence: 99%

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Liu

Wang

2023

Asian J Org Chem

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Ring-fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction of such structures from readily available substrates becomes an important researching topic in organic synthesis. Triggered by the addition of radicals to the (activated or unactivated) double bonds in alkenes, the subsequent intramolecular addition/cyclization leads to polycyclic compounds. Following this procedure, a variety of functionalized ring-fused structures were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, and operational simple approaches toward versatile functionalized polycyclic structures from readily available alkene-based substrates.Here, we summarized the recent achievements on the formation of ring-fused polycyclic structures via the radicaltriggered cascade reactions of alkenes. Construction of polycyclic structures with no less than 3 fused rings developed during the last decade were included in this Review, corresponding mechanisms were also discussed.

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Section: Cyclization Of Alkene-tethered 2-arylindoles and 2-aryl Benz...mentioning

confidence: 99%

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Liu

Wang

2023

Asian J Org Chem

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“…Since 2014, modifying the reaction conditions has allowed for several different difunctionalization reactions of alkenes through the denitrogenative radical generation of carbazates. The subsequent radical has been shown to undergo coupling with oxygen sources like peroxides [ 114 – 115 ] and air [ 116 ].…”

Section: Reviewmentioning

confidence: 99%

Iron-catalyzed domino coupling reactions of π-systems

Pounder¹,

Tam²

2021

Beilstein J. Org. Chem.

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The development of environmentally benign, inexpensive, and earth-abundant metal catalysts is desirable from both an ecological and economic standpoint. Certainly, in the past couple decades, iron has become a key player in the development of sustainable coupling chemistry and has become an indispensable tool in organic synthesis. Over the last ten years, organic chemistry has witnessed substantial improvements in efficient synthesis because of domino reactions. These protocols are more atom-economic, produce less waste, and demand less time compared to a classical stepwise reaction. Although iron-catalyzed domino reactions require a mindset that differs from the more routine noble-metal, homogenous iron catalysis they bear the chance to enable coupling reactions that rival that of noble-metal-catalysis. This review provides an overview of iron-catalyzed domino coupling reactions of π-systems. The classifications and reactivity paradigms examined should assist readers and provide guidance for the design of novel domino reactions.

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Transition‐Metal‐Free Radical Cyclization of 2‐Arylbenzoimidazoles with Unactivated AlkanesviaC(sp³)−H Functionalizations in Aqueous Media

Mei

Cai

et al. 2022

Adv Synth Catal

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Here we present a transition-metal-free radical cyclization of 2-arylbenzoimidazoles with unactivated alkanes. By using di-tert-butyl peroxide (DTBP) to promote the C(sp 3 )À H bond functionalization, this approach enables assembly of various benzimidazo[2,1-a]isoquinolin-6(5H)-ones in aqueous media. This strategy can not only well tolerate a wide range of cyclic alkanes, straight-chain alkanes, toluene derivatives, as well as pharmaceutical molecule eudesmol, but also provides an approach for the functionalization of unactivated C(sp 3 )À H bonds in aqueous media under transition-metal-free systems.

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Iron-Catalyzed Oxidative Radical Alkoxycarbonylation of Activated Alkenes with Carbazates toward Alkoxycarbonylated Benzimidazo[2,1-a]isoquinolin-6(5H)-ones

Cited by 11 publications

References 5 publications

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Iron-catalyzed domino coupling reactions of π-systems

Transition‐Metal‐Free Radical Cyclization of 2‐Arylbenzoimidazoles with Unactivated AlkanesviaC(sp³)−H Functionalizations in Aqueous Media

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Iron-Catalyzed Oxidative Radical Alkoxycarbonylation of Activated Alkenes with Carbazates toward Alkoxycarbonylated Benzimidazo[2,1-a]isoquinolin-6(5H)-ones

Cited by 11 publications

References 5 publications

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Iron-catalyzed domino coupling reactions of π-systems

Transition‐Metal‐Free Radical Cyclization of 2‐Arylbenzoimidazoles with Unactivated AlkanesviaC(sp3)−H Functionalizations in Aqueous Media

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Product

Resources

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Transition‐Metal‐Free Radical Cyclization of 2‐Arylbenzoimidazoles with Unactivated AlkanesviaC(sp³)−H Functionalizations in Aqueous Media