Visible‐Light‐Mediated Functionalization of Aryl Diazonium Salts

Zhang, Xin; Mei, Yaoyao; Li, Yangyang; Hu, Jingang; Huang, Dayun; Bi, Yicheng

doi:10.1002/ajoc.202000636

Cited by 33 publications

(17 citation statements)

References 77 publications

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“…25 There are extensive studies on photocatalyzed arylation reactions. 26,27 Metal-free photocatalytic arylations 28 have been reported with numerous photocatalysts, such as carbon nitride-based catalysts. 30 A few examples of photocatalytic arylations in aqueous media have been informed.…”

Section: ■ Photocatalyzed Substitutions Of Arenes In Aqueous Mediamentioning

confidence: 99%

“…Radical arylation reactions are synthetic strategies that allow the formation of new C Ar –C Ar bonds or C aliph –C Ar bonds from aryl radicals . There are extensive studies on photocatalyzed arylation reactions. , Metal-free photocatalytic arylations have been reported with numerous photocatalysts, such as carbon nitride-based catalysts …”

Section: Photocatalyzed Substitutions Of Arenes In Aqueous Mediamentioning

confidence: 99%

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Advances in Photocatalytic Organic Synthetic Transformations in Water and Aqueous Media

Barata‐Vallejo

Yerien

Postigo

2021

ACS Sustainable Chem. Eng.

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Advances in visible light-photocatalyzed preparative synthetic organic transformations in water or aqueous media are studied. Both the convenience of visible light photocatalytic strategies to achieve synthetic organic transformations and the employment of water or aqueous mixtures make this approach a very resourceful methodology. Mechanistic aspects for such photocatalyzed processes are discussed. The effects of water in the stereoselectivity of some reactions and considerations regarding the improved enantioselectivity in chiral catalytic photoredox reactions are manifested with the use of water. The use of water as a result of a protocol improvement or environmentally friendlier methodology as compared to the same reaction performed in organic solvents are also considered. All these combined effects of water as a reaction medium or its very presence in photocatalytic reactions have an ultimate goal which is to diminish the environmental impact of synthetic and photocatalytic processes. This perspective highlights the progress and state of the art organic transformations realized by photocatalytic techniques in water or aqueous systems as well as water as a reactant. In this regard, aromatic substitution reactions, radical additions to carbon–carbon double bonds, photooxidation reactions, decarboxylation processes, and miscellaneous reactions are presented.

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Section: ■ Photocatalyzed Substitutions Of Arenes In Aqueous Mediamentioning

confidence: 99%

Section: Photocatalyzed Substitutions Of Arenes In Aqueous Mediamentioning

confidence: 99%

Advances in Photocatalytic Organic Synthetic Transformations in Water and Aqueous Media

Barata‐Vallejo

Yerien

Postigo

2021

ACS Sustainable Chem. Eng.

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“…Visible-light-driven arylation provides a cheap, efficient, and environmentally safe method, which is the research focus in recent years. An enormous amount of literature for visible-light-driven photocatalytic reduction of aromatic compounds to prepare aryl radicals under mild conditions has been reported [ 6 , 7 , 8 , 9 , 10 , 11 ]. For example, König summarized visible-light-driven arylation reactions of aryl diazonium salts, aryl iodonium salts, aryl halides, and other substrates [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

“…For example, König summarized visible-light-driven arylation reactions of aryl diazonium salts, aryl iodonium salts, aryl halides, and other substrates [ 7 ]. Huang reviewed the reactions of aryl diazonium salts as substrates to construct C-C, C-B, C-N, C-S and C-P bonds under visible light conditions [ 10 ]. Kvasovs and Gevorgyan reviewed the photocatalytic systems for the photocatalytic generation of aryl radicals using aryl diazonium salts, aryl halides, aryl triflates, and aryl carboxylic acids as precursors and presented their modern application examples [ 11 ].…”

Section: Introductionmentioning

confidence: 99%

Visible-Light Photocatalytic Reduction of Aryl Halides as a Source of Aryl Radicals

et al. 2022

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Aryl- and heteroaryl units are present in a wide variety of natural products, pharmaceuticals, and functional materials. The method for reduction of aryl halides with ubiquitous distribution is highly sought after for late-stage construction of various aromatic compounds. The visible-light-driven reduction of aryl halides to aryl radicals by electron transfer provides an efficient, simple, and environmentally friendly method for the construction of aromatic compounds. This review summarizes the recent progress in the generation of aryl radicals by visible-light-driven reduction of aryl halides with metal complexes, organic compounds, semiconductors as catalysts, and alkali-assisted reaction system. The ability and mechanism of reduction of aromatic halides in various visible light induced systems are summarized, intending to illustrate a comprehensive introduction of this research topic to the readers.

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“…In the literature, the conversion of C(sp 2 )–NH 2 into radical precursors has been well explored via the synthesis of diazonium salts, albeit with some limitations in the exploration of aliphatic diazonium salts. 6 Fortunately, other alkyl radical precursors that can be easily generated are the bench-stable Katritzky pyridinium salts, which are prepared from the reaction of a primary amine with 2,4,6-triphenyl pyrylium in one step. 7 The use of Katritzky salt as a C-centered radical source was elegantly demonstrated by Watson for a nickel catalysed deaminative Suzuki–Miyaura cross-coupling reaction.…”

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confidence: 99%