Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System

Huang, Jiawei; Li, Xiaoman; Xu, Liang; Yu, Wu

doi:10.1021/acs.joc.2c02856

Cited by 19 publications

(6 citation statements)

References 61 publications

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“…On the basis of these preliminary mechanistic studies and literature precedent, ,, a plausible reaction pathway is proposed in Scheme . First, TBATB decomposes into TBAB and Br 2 , which is converted into hypobromous acid (HOBr).…”

Section: Resultsmentioning

confidence: 99%

One-Pot, Metal-Free Synthesis of Allyl Sulfones in Water

Jia,

Jiang,

Wang

et al. 2024

J. Org. Chem.

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A one-pot dehydration cross-coupling reaction between allyl alcohols and sodium sulfinates that provides allyl sulfones in good to excellent yields is presented. Its broad substrate scope includes symmetrical and asymmetrical α,α-diaryl- and α-aryl-substituted allylic alcohols and aryl and alkyl sodium sulfinates. For asymmetrical allylic substrates, the E isomer predominates with examples of excellent stereoselectivity. Control experiments provide the basis for a proposed radical-mediated mechanism. The metal-free procedure applies cheap and commercially available tetrabutylammonium tribromide as the catalyst and H2O as the solvent. Notable features of this simple, efficient, weakly toxic, and environmentally benign strategy include mild and convenient operating conditions and readily accessible starting materials.

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Section: Resultsmentioning

confidence: 99%

One-Pot, Metal-Free Synthesis of Allyl Sulfones in Water

Jia,

Jiang,

Wang

et al. 2024

J. Org. Chem.

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“…The Wei group [15a] designed a ArSeBr‐mediated protocol, using a catalytic amount of tetrabutylammonium tribromide (TBATB 8.1 ) as the key promoter. By the aid of DMSO, Br 2 was recycled, which was good for the in situ generation of ArSeBr intermediates.…”

Section: Selenylationmentioning

confidence: 99%

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Huang

Wang

et al. 2023

Adv Synth Catal

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Alkenes are valuable feedstocks in organic synthesis. Selenium or sulfur-containing coumpounds with a neighboring functional group can be easily prepared by direct difunctionalization of alkenes via three-component reactions. It will reduce the number of steps and waste generation, and form complicated molecules from simple starting materials. Herein, recent developments (2013-2022) have been summarized via two categories: (1) selenylation via seleniranium intermediates or Se-centered radicals;(2) thiolation with more diverse mechanisms and products Reactions with electron-rich arenes, alcohols, water, acids, NaN 3 , amines, KSCN, and sulfamides, TMSNCS, TMSN 3 , Et 3 N • 3HF, SOCl 2 , HCl, NFSI, t BuONO, pyridinium salts, t BuOOH, ArN 2 BF 4 , CO 2 , CO, O 2 , CF 3 SO 2 Cl, R 2 P(O)À H, (RO) 2 P(O)SH, (RO) 2 P(O)OH et al will be discussed.We hope this review will do help for future research in this area.1. Thiolation 3.1. Synthesis of Sulfides 3.2. Synthesis of Sulfoxides 3.3. Synthesis of Sulfones 4.Conclusions and Outlook

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“…In 2023, Wei′s research team described a selenylation reaction involving olefin, water/alcohol, and diselenide/thiophenol as raw materials in a metal‐free reaction system, [33] which employed tetrabutylammonium tribromide (TBATB) as a catalyst and dimethyl sulfoxide (DMSO) as a terminal oxidant. They synthesized a series of β‐hydroxyl or β‐alkoxy organochalcogenides with yields of 45–98 % (Scheme 12).…”

Section: Difunctionalization Of Olefins With Diselenidesmentioning

confidence: 99%

Advances in Difunctionalization of Olefins with Diorganyl Dichalcogenides

Wang,

Nkingwa,

Islam

et al. 2023

Chemistry An Asian Journal

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Organochalcogen molecules have extensive applications in various fields. They serve as pharmaceuticals, ligands, organocatalysts, agrochemicals, and other functional materials. Difunctionalization of olefins, which belong to a class of multicomponent reactions, is a successful technique for introducing two functional moieties in a single‐step reaction, both in terms of atom economy and step economy. The difunctionalization of olefins with diorganyl dichalcogenides may effectively increase the molecular complexity, which has achieved significant advancements in recent decades. This article describes recent advancements in the difunctionalization of olefins with diorganyl diselenides and diorganyl disulfides.

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Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System

Cited by 19 publications

References 61 publications

One-Pot, Metal-Free Synthesis of Allyl Sulfones in Water

One-Pot, Metal-Free Synthesis of Allyl Sulfones in Water

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Advances in Difunctionalization of Olefins with Diorganyl Dichalcogenides

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