Photochemical Selenosulfonation of Tricyclo[4.1.0.02,7]heptane Derivatives

Kostryukov, S. G.; Masterova, Yu. Yu.; Burtasov, A. A.; Romanova, E. V.

doi:10.1134/s107042802006007x

Cited by 3 publications

(4 citation statements)

References 15 publications

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“…Obviously the antisyn ratio depends on the nature of the R group which influences the inversion rate of radical 38 (Scheme 11). [44] 3.4. 1,3-Addition Reactions 1,3-selenosulfonylation reaction was lacking in the literature since 2021 when Zhou and Li reported for the first time the visible-light-driven addition of compounds 3 to vinyldiazoacetates 40 [45] and, one year later, to alkynyl diazo compounds 41, [46] producing various γ-seleno allylic sulfones 42 and tetrasubstituted allenes 43, respectively (Scheme 12).…”

Section: 2-addition To Allenes and To Cà C Single Bondsmentioning

confidence: 99%

“…Few reports of 1,4-addition reactions encompassing selenosulfones to CÀ C multiple bonds are present in the literature, the one recently reported by Wang and coworkers is worth to mention since it provides a nice example of a rapid, blue LEDinduced entry to build highly substituted sulfonyl carbocyclic and heterocyclic derivatives (compounds 45, Scheme 13) from internal 1,6-diynes (44). The reaction is fast, being complete in less than 30 min and is carried out under environmentally friendly conditions without the need of metals, acids, bases, or heterologous additives.…”

Section: 4-addition Reactionsmentioning

confidence: 99%

“…Obviously the anti‐syn ratio depends on the nature of the R group which influences the inversion rate of radical 38 (Scheme 11). [44] …”

Section: Addition Reactions To C−c Single and Multiple Bondsmentioning

confidence: 99%

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Selenosulfones, a Meetup of Chalcogens: A Journey Into Their Recent Chemistry

Bagnoli,

Rosati,

Marini

et al. 2024

Eur J Org Chem

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A mini review focused on the chemistry of selenosulfones reported since 2019 is here presented. Initially, methods aimed to the preparation of such moiety are discussed. Successively 1,2‐, 1,3‐, 1,4‐ and 1,7‐addition reactions to C‐C single and multiple bonds are illustrated. The third chapter deals with C‐H functionalizations while the fourth one shows the reactions with aryl diazonium salts or its precursors. The radical coupling with redox active reagents, is the subject of section five. Selenosulfones challenged in nucleophilic substitutions and in reactions with phosphorus‐containing compounds are shown in chapter six and seven followed by the conclusions and perspectives section.

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Section: 2-addition To Allenes and To Cà C Single Bondsmentioning

confidence: 99%

Section: 4-addition Reactionsmentioning

confidence: 99%

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Selenosulfones, a Meetup of Chalcogens: A Journey Into Their Recent Chemistry

Bagnoli,

Rosati,

Marini

et al. 2024

Eur J Org Chem

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show abstract

“…Meanwhile, Kostryukov and coworkers reported a photochemical selenosulfonylation of tricyclo[4.1.0.0 2,7 ]heptanes 84a with Se -phenyl selenosulfonates 84b for the synthesis of a series of 6,6,7-trisubstituted bicyclo[3.1.1]heptanes 84c–d with endo -oriented sulfonyl group at C7 and anti - or syn -oriented phenylselanyl substituent at C6 (Scheme 84). 112 The difunctionalization regioselectively occurred at the C1–C7 central bond of tricycloheptanes 84a . Depending on the nature of the X substituent in the initial tricycloheptane, different anti / syn selectivities were observed.…”

Section: Selenosulfonylationmentioning

confidence: 99%

Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization

Wang¹,

Xu²,

Zhou³

et al. 2023

Org. Chem. Front.

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Photoinduced ynamide structural reshuffling and functionalization

Mutra

Wang

2022

Nat Commun

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The radical chemistry of ynamides has recently drawn the attention of synthetic organic chemists to the construction of various N-heterocyclic compounds. Nevertheless, the ynamide-radical chemistry remains a long-standing challenge for chemists due to its high reactivity, undesirable byproducts, severe inherent regio- and chemoselective problems. Importantly, the ynamide C(sp)-N bond fission remains an unsolved challenge. In this paper, we observe Photoinduced radical trigger regio- and chemoselective ynamide bond fission, structural reshuffling and functionalization of 2-alkynyl-ynamides to prepare synthetically inaccessible/challenging chalcogen-substituted indole derivatives with excellent step/atom economy. The key breakthroughs of this work includes, ynamide bond cleavage, divergent radical precursors, broad scope, easy to handle, larger-scale reactions, generation of multiple bonds (N-C(sp2), C(sp2)-C(sp2), C(sp2)-SO2R/C-SR, and C-I/C-Se/C-H) in a few minutes without photocatalysts, metals, oxidants, additives. Control experiments and 13C-labeling experiments supporting the conclusion that sulfone radicals contribute to ynamide structural reshuffling processes via a radical pathway.

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Photochemical Selenosulfonation of Tricyclo[4.1.0.02,7]heptane Derivatives

Cited by 3 publications

References 15 publications

Selenosulfones, a Meetup of Chalcogens: A Journey Into Their Recent Chemistry

Selenosulfones, a Meetup of Chalcogens: A Journey Into Their Recent Chemistry

Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization

Photoinduced ynamide structural reshuffling and functionalization

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