Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach

Bartolomeu, Aloísio de Andrade; Silva, Rodrigo da; Brocksom, Timothy J.; Noël, Timothy; Oliveira, Kléber T. de

doi:10.1021/acs.joc.9b01879

Cited by 40 publications

(36 citation statements)

References 103 publications

(211 reference statements)

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“…In 2019, Bartolomeu et al reported direct CÀ H arylation of pyridines without any photocatalyst using an electron donor-acceptor (EDA) approach under visible light irradiation (Scheme 30). [51] At first, the aryldiazonium salt forms an adduct with pyridine to form the EDA complex. The EDA complex on absorbing the visible light goes to the excited state, which immediately dissociates to form aryl radicals.…”

Section: Direct Cà H Arylation Of Pyridinesmentioning

confidence: 99%

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

et al. 2021

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Aryl diazonium salts are an important class of organic compounds that are now widely used as arylating agents in photoredox catalysis owing to their lower redox potential, broad substrate scope, and atom economy. They have successfully been used in many interesting organic transformations to introduce an aryl group. They serve as good alternatives for aryl halides and other aryl organometallic reagents primarily used as aryl group surrogates. New reactions using aryl diazonium salts are continually emerging, and in this review, we have highlighted some recent developments in photoredox arylations and their applications. 4.3. Oxy-Arylation of Alkynes for the Synthesis of Benzofuran 4.4.

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Section: Direct Cà H Arylation Of Pyridinesmentioning

confidence: 99%

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

et al. 2021

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“…Many reliable methods have been developed that utilized radical addition, elimination, metal‐catalyzed coupling, C−H activation, cyclization or rearrangement. Catalysts like eosin Y, [2,7c 8,19a,21a,26b,27a,30c] Ru(byp) 3 Cl 2 , [3b,5b,d,6c,d,8,16g–i,18a,b,20a,24,27b,28a,b,29] Ru(byp) 3 PF 6 [4b,5a,6a,14,15,28c] were most frequently used. However, challenges still existed: (1) The use of a simple, efficient, and recyclable catalyst system would be advantageous.…”

Section: Discussionmentioning

confidence: 99%

“…Xue [16g] and Oliveira [16h] devised the direct arylation of soluble pyridine hydrochloride with ArN 2 BF 4 by photoredox catalysis in aqueous media. Besides, xanthene, thiazole, pyrazine, and pyridazine were also able to yield arylated products [16g] .…”

Section: C−c Bond Formationmentioning

confidence: 99%

Visible‐Light‐Mediated Functionalization of Aryl Diazonium Salts

Zhang

Mei

et al. 2021

Asian J Org Chem

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Aryl diazonium salts are important molecules in organic chemistry. This review discusses advances of their application in light‐mediated reactions summarized in five categories according to the bond formations: (1) C−C formation from alkenes, alkynes, arenes, isocyanide, CO, arylboronic acid, or Grignard reagent. (2–5) C−B, C−N, C−S, and C−P formations. Reactions such as radical addition, elimination, metal‐catalyzed coupling, C−H activation, cyclizations, and rearrangements will be discussed herein.

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“…In 2019, Oliveira and co-workers used aryldiazonium salt as radical precursors to perform Minisci-type pyridinefunctionalization reaction (Scheme 27). 44 Mechanistic investigations showed that the diazonium salt forms an electron donor-acceptor (EDA) complex with pyridine, and the visible light promotes an electron transfer from the pyridine to the diazonium salt moiety to afford an aryl radical and a pyridinium radical cation after N 2 release. A subsequent Minisci-type process produces the arylated pyridine.…”

Section: Cluster Synlettmentioning

confidence: 99%

Recent Developments in Transition-Metal-Free Functionalization and Derivatization Reactions of Pyridines

Zhou

Jiao²

2020

Synlett

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Pyridine is an important structural motif that is prevalent in natural products, drugs, and materials. Methods that functionalize and derivatize pyridines have gained significant attention. Recently, a large number of transition-metal-free reactions have been developed. In this review, we provide a brief summary of recent advances in transition-metal-free functionalization and derivatization reactions of pyridines, categorized according to their reaction modes.1 Introduction2 Metalated Pyridines as Nucleophiles2.1 Deprotonation2.2 Halogen–Metal exchange3 Activated Pyridines as Electrophiles3.1 Asymmetric 2-Allylation by Chiral Phosphite Catalysis3.2 Activation of Pyridines by a Bifunctional Activating Group3.3 Alkylation of Pyridines by 1,2-Migration3.4 Alkylation of Pyridines by [3+2] Addition3.5 Pyridine Derivatization by Catalytic In Situ Activation Strategies3.6 Reactions via Heterocyclic Phosphonium Salts4 Radical Reactions for Pyridine Functionalization4.1 Pyridine Functionalization through Radical Addition Reactions4.2 Pyridine Functionalization through Radical–Radical Coupling Reactions5 Derivatization of Pyridines through the Formation of Meisenheimer-Type Pyridyl Anions6 Conclusion

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Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach

Cited by 40 publications

References 103 publications

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

Visible‐Light‐Mediated Functionalization of Aryl Diazonium Salts

Recent Developments in Transition-Metal-Free Functionalization and Derivatization Reactions of Pyridines

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