Palladium-Catalyzed Cyclization of Alkenes with Organohalides

Chu, Xiangcheng; Liu, Dan; Zhang, Xing; Xu, Xiaoping; Ji, Shun‐Jun

doi:10.1021/acs.orglett.6b00035

Cited by 18 publications

(4 citation statements)

References 72 publications

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“…In the year 2016, Xu and Ji's group achieved a palladiumcatalyzed cyclization of 2-vinylbiarenes with organohalides as the alkyl radical precursors for the construction of alkylated fluorenes (Scheme 93a). [176] In the same year, they reported a Cu-mediated radical alkylarylation via selective cleavage of the CÀ H bond in alkylnitrile, leading to functionalized fluorene derivatives (Scheme 93b). [177] Moreover, if pyrrole and indole units were used as the aryl motif, polycyclic pyrroloindole derivatives were obtained.…”

Section: Cyclization Of 2-vinylbiarenesmentioning

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 2-vinylbiarenesmentioning

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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“…reported a palladium‐catalyzed synthesis of various fluorene, pyrroloindole, and benzoxazine derivatives through C( sp 2 )−H bond activation and cyclization of alkenes 307 with organohalides 308 (Scheme 87). [63] A series of 2‐aryl olefins bearing electron‐donating groups or electron‐withdrawing groups were subjected to this reaction, affording the corresponding products in moderate to good yields. Additionally, heterocyclic olefins were also compatible with this reaction.…”

Section: Radical Involved Pd‐catalyzed Reactionsmentioning

confidence: 99%

Recent Progress in Palladium‐Catalyzed Radical Reactions

Sun

Liu

et al. 2021

Adv Synth Catal

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In recent years, great improvements have been made on palladium‐catalyzed radical reactions. Emerging elegant methodologies of radical involved palladium‐catalyzed transformations provide more and more effective strategies for the construction of complex heterocyclic compounds and applications in drug discovery. It is universally known that Pd(0)/(II)/(IV)‐mediated reactions usually undergo two‐electron transfer processes, while the Pd(I) and Pd(III) involved reactions usually occur via single electron transfer processes. Since our review on palladium radical was published, numurous methodolgies involving palladium radical have sprung up in the past five years. This review further summarized the up‐to‐date transformations toward palladium radical from 2015. For most of these catalytic cycles strategies, plausible mechanisms are demonstrated in detail to give better insight for chemists in need.

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“…Recently, Ji et al described a Palladium‐catalyzed transformation of 2‐aryl styrene with alkyl halides during a Heck insertion and trapped by an o ‐arylC(sp 2 )‐H bond (Scheme ). Under the optimal reaction conditions, palladium‐catalyzed cyclization of a diversity of alkenes with an array of organohalides afforded the desired fluorene and heterofluorene derivatives in 25–86 % yields.…”

Section: Using Metal Catalysismentioning

confidence: 99%

Recent Developments in Radical‐Mediated Transformations of Organohalides

Lekkala

Balakrishna

et al. 2019

Eur J Org Chem

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In recent years, radical‐mediated transformations of organohalides, a class of powerful chemical transformations, have become an important field at the forefront of organic chemistry. Formation of free‐radicals from organohalides is among the most useful methods to access open‐shell reactive intermediates that have a number of established applications in chemical synthesis. Herein we summarize most of the strategies involving metal‐catalyzed, non‐metal‐catalyzed, as well as catalyst‐free radical‐mediated transformations of organohalides.

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Palladium-Catalyzed Cyclization of Alkenes with Organohalides

Cited by 18 publications

References 72 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

Recent Progress in Palladium‐Catalyzed Radical Reactions

Recent Developments in Radical‐Mediated Transformations of Organohalides

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