Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)

Luo, Anping; Zhang, Min; Fu, Zhangyi; Lan, Jingbo; Wu, Di; You, Jingsong

doi:10.3762/bjoc.16.49

Cited by 10 publications

(6 citation statements)

References 33 publications

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“…The desired product 37c was obtained through a plausible six-membered metalacyclic intermediate 37d, followed by aryl migration. You et al revealed [103] an example of Cu-catalyzed C9 arylation of pyrene-1-carboxamide (37e) with mesityl(phenyl)iodonium triflate (37f) through a bidentate 8-aminoquinoline system, affording 37g (Scheme 30). Substrate N-(tert-butyl)pyrene-1-carboxamide 37e was treated with mesityl(phenyl)iodonium triflate in the presence of Cu(OTf) 2 (10 mol%) in 1,2-dichloroethane at 70 • C for 24 h. This reaction afforded the C(9)-arylated pyrene-1-carboxamide derivative 37g of 65%.…”

Section: Directing Group-assisted C-h Functionalization Of the C9 Pos...mentioning

confidence: 99%

Recent Advances in C–H Functionalization of Pyrenes

Arulananda Babu,

Dalal,

Bodak

2023

Chemistry

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In recent years, transition metal-catalyzed C–H activation and site-selective functionalization have been considered to be valuable synthetic tactics to functionalize organic compounds containing multiple C–H bonds. Pyrene is one of the privileged and notorious polycyclic aromatic hydrocarbons. Pyrene and its derivatives have found applications in various branches of chemical sciences, including organic chemistry, chemical biology, supramolecular sciences, and material sciences. Given the importance of pyrene derivatives, several classical methods, including the C–H functionalization method, have been developed for synthesizing modified pyrene scaffolds. This review attempts to cover the recent developments in the area pertaining to the modification of the pyrene motif through the C–H activation process and the functionalization of C–H bonds present in the pyrene motif, leading to functionalized pyrenes.

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Section: Directing Group-assisted C-h Functionalization Of the C9 Pos...mentioning

confidence: 99%

Recent Advances in C–H Functionalization of Pyrenes

Arulananda Babu,

Dalal,

Bodak

2023

Chemistry

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“…Very recently, You and co-workers extended the concept of copper-catalyzed meta C−H arylation of amine derivatives and aryl acetic acid derivatives for the remote C−H arylation of substituted polycyclic aromatic hydrocarbons (PAHs) like substituted 1-napthamides phenanthrene-9-carboxamide, pyrene-1-carboxamide, and fluoranthene-3-carboxamide, among others, using aryliodonium salts as the arylating agent (Scheme 41). 122 The protocol was not only limited to the amide directing group; additionally, their ketone derivatives were found to be suitable for the C−H arylation with moderate yields. The reaction proceeded through a similar pathway as proposed by Wu, Li, and their co-workers.…”

Section: C−h Alkylation Since the Pioneering Work On The [Ru]-catalyz...mentioning

confidence: 99%

Weak-Coordination in C–H Bond Functionalizations Catalyzed by 3d Metals

2022

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Transition-metal-catalyzed C–H bond functionalizations have had an enormous influence on organic synthesis in recent times. However, the use of low-abundance 4d and 5d metals is almost inevitable, and they are in high demand. This will be a cause of concern, and hence, it is important to develop methods based on 3d metals, which are widely present in the Earth’s crust. In this regard, the use of 3d metal catalysts or their precursors for catalysis, in general, and C–H bond functionalizations, in particular, has gained significant momentum in the recent times. The major development in catalytic C–H bond functionalizations with 3d metals has been achieved predominantly with strongly coordinating directing groups such as pyridyl, pyrimidinyl, pyrazolyl, and 8-amino-quinolinyl groups. Thus, prefunctionalization of substrates with these directing groups is necessary, which contradicts the step- and atom-economy of C–H bond activation. However, commonly available functional groups such as aldehyde, ketone, carboxylic acid, amide, hydroxy, and N-oxides loosely bind to metals through weak-coordination. These weakly coordinating directing groups orient the metal to activate C–H bond regioselectively without the need for preinstalled strongly coordinating directing groups. Although it is challenging, this contemporary topic has been actively pursued by many researchers in recent times. Through this article, we provide a comprehensive overview of 3d metal-catalyzed, weakly coordinating, directing-group-enabled C–H bond functionalizations reported until March 2021.

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“…In 2020, You research group has reported Cu(II)‐Catalyzed C‐7 arylation of polyaromatic hydrocarbons employing title electrophile (Scheme 26). [58] The C‐7 arylation of different N ‐( tert ‐butyl)‐1‐naphthamide was performed with unsymmetrical iodonium triflate using 10 mol % Cu(OTf) 2 in DCE at 70 °C. The yields of arylation were influenced by electronic effects as well as the steric effect of diverse aryliodonium salts based on the substituents on the aryl ring.…”

Section: C(sp2)−h Arylation Reactionmentioning

confidence: 99%

Diaryliodonium Salts in Transition‐Metal‐Catalyzed Chelation‐Induced C(sp²/sp³)−H Arylations

Joshi

2021

Eur J Org Chem

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Transition-metal-catalyzed Cross-coupling via directing group assisted CÀ H bond activation has become an expedient tool in current synthesis to achieve diverse molecular complexity. In this context, chelation-assisted arylations of C(sp 2 /sp 3)À H bonds have been extensively investigated as aryl/biaryl derivatives are an important contributor in the area of the industry, farming, medicinal and material science. The diaryliodonium salt has been broadly utilized in C(sp 2 /sp 3)À H bond arylation where the reaction proceeds via oxidative addition of aryliodonium salt to chelation induced metallacycle. The proximal/remote C(sp 2 / sp 3)À H bonds in coordination with transition metals are arylated by a range of directing groups in good to excellent yields. In this mini-review, we have outlined the up to date developments on transition-metal-catalyzed chelation assisted C(sp 2 /sp 3)À H bond arylation utilizing diaryliodonium salts as the coupling partner.

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Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)

Cited by 10 publications

References 33 publications

Recent Advances in C–H Functionalization of Pyrenes

Recent Advances in C–H Functionalization of Pyrenes

Weak-Coordination in C–H Bond Functionalizations Catalyzed by 3d Metals

Diaryliodonium Salts in Transition‐Metal‐Catalyzed Chelation‐Induced C(sp²/sp³)−H Arylations

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Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)

Cited by 10 publications

References 33 publications

Recent Advances in C–H Functionalization of Pyrenes

Recent Advances in C–H Functionalization of Pyrenes

Weak-Coordination in C–H Bond Functionalizations Catalyzed by 3d Metals

Diaryliodonium Salts in Transition‐Metal‐Catalyzed Chelation‐Induced C(sp2/sp3)−H Arylations

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Diaryliodonium Salts in Transition‐Metal‐Catalyzed Chelation‐Induced C(sp²/sp³)−H Arylations