Rongalite in PEG-400 as a general and reusable system for the synthesis of 2,5-disubstituted chalcogenophenes

Schneider, Paulo H.; Paixão, Douglas Bernardo; Soares, Eduardo G. O.; Salles, Helena Domingues de; Silva, Caren Daniele Galeano da; Rampon, Daniel S.

doi:10.1039/d2qo01069k

Cited by 11 publications

(9 citation statements)

References 147 publications

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“…On the basis of the results of the control experiments and previous reports, − we propose a plausible mechanism (Scheme ). First, a direct nucleophilic substitution process between 1 and 2 happens to yield species A , which further undergoes dehydration with the assistance of NaOAc to give intermediate B .…”

supporting

confidence: 57%

Synthesis of Tetrahydro-2H-thiopyran 1,1-Dioxides via [1+1+1+1+1+1] Annulation: An Unconventional Usage of a Tethered C–S Synthon

Chen

Wang

et al. 2022

Org. Lett.

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An unprecedented [1+1+1+1+1+1] annulation process has been developed for the construction of tetrahydro-2H-thiopyran 1,1-dioxides. Notably, rongalite acted as a tethered C–S synthon in this reaction and can be chemoselectively used as triple C1 units and as a source of sulfone. Mechanistic investigation indicated that two different carbon-increasing models are involved in this reaction in which rongalite serves as C1 units.

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supporting

confidence: 57%

Synthesis of Tetrahydro-2H-thiopyran 1,1-Dioxides via [1+1+1+1+1+1] Annulation: An Unconventional Usage of a Tethered C–S Synthon

Chen

Wang

et al. 2022

Org. Lett.

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“…Remarkably, 2,5-disubstituted chalcogenophenes from 1,3butadiynes and elemental chalcogens (Te, S, Se) using rongalite in PEG-400, have successfully been reported by the research team of Schneider (scheme 3). [14] In this method, chalcogen species -acting as the nucleophiles were added regioselectively to the triple bond, which upon subsequent cyclization in 5endo-dig manner afforded a wide variety of the corresponding chacogenophenes. In this study, the authors have employed diverse symmetrical as well as non-symmetrical 1,3-butadiynes consisting of both electron-donating groups (EDGs) as well as electron-withdrawing groups (EWGs).…”

Section: Organochalcogen (S Se Te) Compoundsmentioning

confidence: 99%

Recent Developments in Rongalite Chemistry: A Critical Review

Ali

2023

ChemistrySelect

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Rongalite whose chemical structure was discovered in 1905, is an inexpensive, easily assessable, and copious industrial product, which has significantly been used for a long time in rubber, dye, and veterinary industries. Moreover, it has also been used as an antidote against several heavy metals poisoning, in addition to its applications in the photographic developer and veterinary medicines. Gratifyingly, Rongalite has also shown its uses as the fungicidal, bactericidal and antioxidant in pharmaceutical formulation. Besides, it has also been used in material sciences, and also as a viable cosmetic hair‐dye‐color removers. Interestingly, in past decade, it has shown its high‐impact in the arena of synthetic organic chemistry serving as SO22− equivalent, C1 synthon donor, reducing agent/radical initiator or proton source ‐ to assemble diverse intricate organic molecules under operationally simple yet efficient conditions. However, the services of multiple features of Rongalite in synthetic chemistry are still at the research stage, and needs to be sophisticated to a higher level in many years to come. Considering the synthetic importance of this valued reagent, this review article presents the advancement made in the field of Rongalite chemistry in the past three years. This review article will update the researchers working in this arena about the advancement of Rongalite in the synthetic organic transformations as well as it will help readers wishing to deal with this easy‐to handle and eco‐friendly low‐cost commodity chemical. This review article updating the rongalite chemistry will be useful to the chemical community in general and synthetic chemists in particular.

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“…In the last decades, chalcogens (O, S, Se, and Te) have received great attention for applications in materials. 16,17 Recently, Silveira and collaborators 18 synthesized a series of organoselenium compounds with photophysical properties UV-Vis and steady-state emission fluorescence. In the UV-Vis study, for example, all derivatives revealed transition bands in the ultraviolet and visible window between 270 and 450 nm.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of photophysical, electrochemical, and ROS generation properties of new chalcogen-naphthoquinones-1,2,3-triazole hybrids

Gomes,

Costa,

Duarte

et al. 2023

RSC Adv.

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Rongalite in PEG-400 as a general and reusable system for the synthesis of 2,5-disubstituted chalcogenophenes

Abstract: In this work, we report the use of rongalite in PEG-400 as a general, reusable, efficient, inexpensive and environmentally benign reductive system for elemental chalcogens and its use for the...

Cited by 11 publications

References 147 publications

Synthesis of Tetrahydro-2H-thiopyran 1,1-Dioxides via [1+1+1+1+1+1] Annulation: An Unconventional Usage of a Tethered C–S Synthon

Synthesis of Tetrahydro-2H-thiopyran 1,1-Dioxides via [1+1+1+1+1+1] Annulation: An Unconventional Usage of a Tethered C–S Synthon

Recent Developments in Rongalite Chemistry: A Critical Review

Synthesis and evaluation of photophysical, electrochemical, and ROS generation properties of new chalcogen-naphthoquinones-1,2,3-triazole hybrids

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