Beyond classical sulfone chemistry: metal- and photocatalytic approaches for C–S bond functionalization of sulfones

Corpas, Javier; Kim‐Lee, Shin‐Ho; Mauleón, Pablo; Arrayás, Ramón Goméz; Carretero, Juan C.

doi:10.1039/d0cs00535e

Cited by 58 publications

(32 citation statements)

References 302 publications

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“… , In addition, the sulfone moiety is an important synthetic target and widely used as a versatile synthetic intermediate for organic chemistry. Therefore, many synthetic methodologies have been developed for the preparation of sulfones, for example, oxidation of sulfides, Friedel-Crafts-type sulfonation with sulfonyl halides, and coupling of sulfinic acid salts. − …”

Section: Introductionmentioning

confidence: 99%

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Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids

Yao

Xie

et al. 2023

J. Org. Chem.

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A simple and efficient electrochemical sulfonylation of organoboronic acids with sodium arylsulfinate salts has been reported for the first time. A variety of aryl, heteroaryl, and alkenylsulfones were obtained in good to excellent yields via a simple electrochemical sulfonylation of various arylboronic acids, heterocyclic boronic acids, or alkenylboronic acids with sodium arylsulfinate at room temperature in 5 h under the catalyst-free and additive-free conditions. A plausible mechanism has been proposed based on various radical-trapping and CV control experiments.

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Section: Introductionmentioning

confidence: 99%

“…3 CN/ H 2 O as mixed solvents, carbon electrode as the anode, platinum electrode as the cathode, and a constant current of 15 mA (…”

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confidence: 99%

Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids

Yao

Xie

et al. 2023

J. Org. Chem.

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“…To achieve this, we envisioned that an appropriate base metal catalyst can be exploited to activate the aromatic reaction partner, in order to promote efficient desulfonylative CÀ C cross-coupling with the sulfone. A potential complication that may arise is the site selectivity of sulfone activation, since transition metals are known to insert into C(sp 2 )À S bonds within aryl/alkenyl sulfones [35][36][37] leading to undesired products. Herein, we disclose a series of versatile Fe-or Nicatalyzed transformations that address the aforementioned challenges (Scheme 2b).…”

Section: Introductionmentioning

confidence: 99%

StereoselectiveC‐Aryl Glycosylation by Catalytic Cross‐Coupling of Heteroaryl Glycosyl Sulfones

et al. 2023

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Stereoselective C‐glycosylation reactions are increasingly gaining attention in carbohydrate chemistry because they enable glycosyl precursors, readily accessible as anomeric mixtures, to converge to a single diastereomeric product. However, controlling the stereochemical outcome through transition‐metal catalysis remains challenging, and methods that leverage bench‐stable heteroaryl glycosyl sulfone donors to facilitate glycosylation are rare. Herein, we show two complementary nonprecious metal catalytic systems, based on iron or nickel, which are capable of promoting efficient C−C coupling between heteroaryl glycosyl sulfones and aromatic nucleophiles or electrophiles through distinct mechanisms and modes of activation. Diverse C‐aryl glycosides were secured with excellent selectivity, scope, and functional‐group compatibility, and reliable access to both α and β isomers was possible for key sugar residues.

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“…1a) (Buynak et al 2000; Sravya et al 2019;Sravya et al 2016). Moreover, allylic sulfones can also serve as a kind of versatile building block to construct many complex organic molecules (Corpas et al 2022;Nambo et al 2022). Owning to their precious applications, tremendous efforts have been devoted to the exploration of e cient synthetic methods for allylic sulfones all along (Chu et and Zi (Zhang et al 2020) reported palladium-catalysed hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides and sul nic acid respectively (Fig.…”

Section: Introductionmentioning

confidence: 99%

Transition-Metal-Free Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Efficient Approach to Branched Allylic Sulfones

Chang

Chen

Zhang

et al. 2022

Preprint

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Branched allylic sulfones are privileged scaffolds widely distributed in bioactive molecules, and organic functional materials. Some methods for the synthesis of allyl sulfones have been developed, such as Tsuji-Prost reaction, hydrosulfonylation and radical addition reactions. Despite these advances, the transition-metal-free hydrosulfonylation of unactive 1,3-diene leading to branched allylic sulfones has rarely explored. Herein, a boron-catalysed highly regioselective hydrosulfonylation of 1,3-diene with sulfinic acid has been explored to construct a broad scope of branched allylic sulfones. The reactions proceed smoothly without the help of transition-metal-catalyst. Abundant structural motifs have also been obtained through simple transformation from the generated allylic sulfone products. Compared with the previous methods, this protocol exhibited advantages as following: 1) readily available starting material without pre-treatment; 2) under the catalysis of inexpensive boron trifluoride etherate, avoidance of transition-metal-catalyst; 3) simple operation and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger; 4) excellent atom economy and regioselectivity.

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Beyond classical sulfone chemistry: metal- and photocatalytic approaches for C–S bond functionalization of sulfones

Abstract: Sulfones are excellent candidates for the design of new C–C and C–X bond-forming reactions owing to the easy activation of C–S bonds. This review focuses on challenges and recent opportunities for catalytic functionalization of sulfones.

Cited by 58 publications

References 302 publications

Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids

Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids

StereoselectiveC‐Aryl Glycosylation by Catalytic Cross‐Coupling of Heteroaryl Glycosyl Sulfones

Transition-Metal-Free Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Efficient Approach to Branched Allylic Sulfones

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