Heterogeneous Carbon Nitrides Photocatalysis Multicomponent Hydrosulfonylation of Alkynes To Access β-Keto Sulfones with the Insertion of Sulfur Dioxide in Aerobic Aqueous Medium

Ni, Bangqing; Zhang, Binbin; Han, Jian; Peng, Bohan; Shan, Yuling; Niu, Tengfei

doi:10.1021/acs.orglett.9b04454

Cited by 67 publications

(30 citation statements)

References 74 publications

(19 reference statements)

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“…Very recently in 2020, Niu and his group [98] demonstrated a method for oxosulfonylation of alkynes to prepare β ‐keto sulfones under solar light or Xe lamp (250 W) irradiation. However, they have introduced a new, cheap, metal‐free, non‐toxic and easily recyclable graphitic carbon nitride (p‐g‐C 3 N 4 ) photocatalyst for this transformation.…”

Section: Different Oxosulfonylation Methodsmentioning

confidence: 99%

Advances in Oxosulfonylation Reaction

et al. 2020

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Oxosulfonylation is a difunctionalization protocol where oxo and sulfonyl groups are introduced in one step to construct ketosulfones and Nacylsulfonamides from simple and readily accessible reagents. The development of oxosulfonylation methods has gained significant attention due to their importance in organic and medicinal chemistry. This review article provides a brief and concise overview of the current status and latest methodologies using green oxidant and sulfonyl sources for oxosulfonylation reactions developed in the last two decades.

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Section: Different Oxosulfonylation Methodsmentioning

confidence: 99%

Advances in Oxosulfonylation Reaction

et al. 2020

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“…Another methodology to access β-ketosulfones 100 was proposed by the groups of Ni and Niu in 2020 (Scheme 37). 54 Hydrosulfonylation of alkynes 99 is attained under aerobic conditions exploiting graphitic carbon nitride p-g-C3N4 as the photocatalyst. This catalyst is not only cheap, highly stable to temperature and light but it can be easily recycled.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…In 2020, Ni and Niu used the hydrosulfonylation of alkynes 99 under aerobic conditions exploiting graphitic carbon nitride p-g-C 3 N 4 as the photocatalyst to obtain keto sulfones 100 (Scheme 37). 54 Graphitic carbon nitride p-g-C 3 N 4 is not only cheap and highly stable to temperature and light, but also it can be easily recycled. 55 The starting materials employed were alkynes 99, arenediazonium tetrafluoroborates 32, and DABCO•(SO 2 ) 2 .…”

Section: Scheme 36 Light-mediated Sulfonylation In the Presence Of The Katritzky Salts As Radical Precursorsmentioning

confidence: 99%

Visible Light as the Key for the Formation of Carbon–Sulfur Bonds in Sulfones, Thioethers, and Sulfonamides: An Update

Azzi¹,

Lanfranco²,

Moro³

et al. 2021

Synthesis

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This review summarizes the most relevant advancements made in the photocatalyzed synthesis of sulfones, thioethers and sulfonamides from 2017 to the beginning of 2021. Synthetic strategies towards the construction of sulfur-carbon bonds are discussed together with the proposed reaction mechanisms. Interestingly, sulfured-based functional groups, which are of fundamental importance for the pharmaceutical field, can be assembled by photocatalysis in an easy and straightforward way in milder reaction conditions employing less toxic and expensive sulfur sources in comparison with common strategies

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“…The reaction process is similar to that presented in Scheme 14. The Nie and Niu group reported the preparation of β-ketosulfones 52 via graphiti carbon nitride (p-g-C3N4)-photocatalyzed hydrosulfonylation of alkynes in aerobic aque ous medium (Scheme 31) [54]. The heterogeneous semiconductor is recyclable at least times without significant reducing activity.…”

Section: Scheme 31 Light-promoted Hydrosulfonylation Of Arylalkynesmentioning

confidence: 99%

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

Yao

Zhang

2020

Molecules

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Popular and readily available alkenes and alkynes are good substrates for the preparation of functionalized molecules through radical and/or ionic addition reactions. Difunctionalization is a topic of current interest due to its high efficiency, substrate versatility, and operational simplicity. Presented in this article are radical addition followed by oxidation and nucleophilic addition reactions for difunctionalization of alkenes or alkynes. The difunctionalization could be accomplished through 1,2-addition (vicinal) and 1,n-addition (distal or remote) if H-atom or group-transfer is involved in the reaction process. A wide range of moieties, such as alkyl (R), perfluoroalkyl (Rf), aryl (Ar), hydroxy (OH), alkoxy (OR), acetatic (O2CR), halogenic (X), amino (NR2), azido (N3), cyano (CN), as well as sulfur- and phosphorous-containing groups can be incorporated through the difunctionalization reactions. Radicals generated from peroxides or single electron transfer (SET) agents, under photoredox or electrochemical reactions are employed for the reactions.

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Heterogeneous Carbon Nitrides Photocatalysis Multicomponent Hydrosulfonylation of Alkynes To Access β-Keto Sulfones with the Insertion of Sulfur Dioxide in Aerobic Aqueous Medium

Cited by 67 publications

References 74 publications

Advances in Oxosulfonylation Reaction

Advances in Oxosulfonylation Reaction

Visible Light as the Key for the Formation of Carbon–Sulfur Bonds in Sulfones, Thioethers, and Sulfonamides: An Update

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

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