“The green side of the moon: ecofriendly aspects of organoselenium chemistry”

Santoro, Stefano; Azeredo, Juliano B.; Nascimento, Vanessa; Sancineto, Luca; Braga, Antônio L.; Santi, Claudio

doi:10.1039/c4ra04493b

Cited by 176 publications

(64 citation statements)

References 153 publications

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“…In this context, the procedure reported by Thomson et al . has been widely used in various organochalcogen transformation reactions– as a source of Na 2 Se 2 . When freshly prepared 5‐alkyl‐2‐chloro‐1‐formyl‐3‐hydroxymethylenecyclohexenes {alkyl= H ( 22 ), Me ( 23 )}, were treated with in situ generated Na 2 Se 2 in presence of hexamethylphosphoramide (HMPA) in THF under reflux condition and the reaction time was extended from 7 h to 18 h, in addition to the expected 1,6‐dioxa‐6a‐selenapentalene, 11 and 1‐oxa‐6,6aλ 4 ‐diselenapentalene, 12 , a third product appeared as the prominent fraction (as monitored by thin layer chromatography).…”

Section: Resultsmentioning

confidence: 99%

Contrasting Reactivity of 2‐chloro‐1‐formyl‐3‐hydroxymethylenecyclohexene and its Schiff Bases towards Disodium Diselenide: Isolation of Selenospirocycles versus Azapentalenes

et al. 2018

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A convenient approach for the synthesis of alicyclic selenospirocycles, 24 and 25, stabilized by intramolecular chalcogen bonding (IChB) is reported by the reaction of 5alkyl-2-chloro-1-formyl-3-hydroxymethylenecyclohexene derivatives {alkyl = H (22), Me (23)} with in situ generated disodium diselenide (Na 2 Se 2 ). However, when 2-chloro-1formyl-3-hydroxymethylenecyclohexene, 22 is condensed with aniline or 4-methoxyaniline and the resulting Schiff bases 26 and 27 are subjected to identical reactions, the Schiff bases undergo cyclisation to afford brightly colored, fused 1,6-diaza-6a-selenapentalene derivatives 28-29, instead of the expected selenospirocycles. The aromatic nucleophilic substitution (S N Ar) reaction of N-(2-bromo-3-nitrobenzyl) naphthylamine, 33 with n BuSeLi affords N-[2-(butylselanyl)-3nitrobenzyl]naphthylamine, 34. The bromination of 34 results in the formation of cyclic isoselenazolines, 35. Selenospirocycles 24 and 25, 1,6-diaza-6a-selenapentalenes 28 and 29 and isoselenazoline 35 are authenticated by single-crystal Xray diffraction studies. Compounds 24, 25 and 35 are stabilized by intramolecular secondary interactions.[a] Dr. Se NMR resonance appears at 931 ppm which is in close agreement with the reported isoselenazoline derivatives. [5] UV-Visible StudiesThe UV-visible studies for ligand 26 and heterocycles 28, 30 were recorded at 15 × 10 À 6 M concentration in acetonitrile as solvent at the room temperature ( Figure 5). All the compounds Figure 4. Plausible mechanism for the formation of 30. Scheme 5. Synthesis of isoselenazoline 35.

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Section: Resultsmentioning

confidence: 99%

Contrasting Reactivity of 2‐chloro‐1‐formyl‐3‐hydroxymethylenecyclohexene and its Schiff Bases towards Disodium Diselenide: Isolation of Selenospirocycles versus Azapentalenes

et al. 2018

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“…Given the continuous interest around the synthesis, the reactivity, and the biological properties of organochalcogen compounds and continuing our ongoing studies on the development of new ecofriendly protocols for the selenenylation of organic substrates, we investigated a new strategy for the preparation of selenoesters [1][2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Reaction of Acyl Chlorides withIn SituFormed Zinc Selenolates: Synthesis of SelenoestersversusRing-Opening Reaction of Tetrahydrofuran

Bellino

Scisciani

Vargas

et al. 2016

Journal of Chemistry

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Attempting to apply thein situproduction of PhSeZnSePh to the synthesis of selenoesters, an unexpected reaction involving the solvent (tetrahydrofuran) was observed and studied. We reported here some evidences about the mechanism and the possibility to control the chemoselectivity of this new reaction that afforded the formation of interesting selenoderivatives in which the selenium moiety and the carboxylic one are spaced by four carbon units.

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“…These opened the way for a series of applications designed in order to address the principle of Green Chemistry, and a number of interesting results obtained during the last five years were recently collected in a review article [1].…”

Section: Water As An Alternative Medium For Organoselenium-catalyzed mentioning

confidence: 99%

“…Water is the natural medium for all biochemical reactions and is often claimed as an ideal green solvent [1,2] because it is non-toxic and non-flammable, has a high heat capacity in adsorbing the energy produced during a chemical reaction, and has low cost and large availability. Breslow [3], Sharpless [4], and several other authors [5] reported reactions that can be efficiently conducted "in-water" or "on-water" conditions.…”

Section: Introductionmentioning

confidence: 99%

Water and Aqueous Mixtures as Convenient Alternative Media for Organoselenium Chemistry

et al. 2016

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Abstract:Even if water is the natural environment for bioorganic reactions, its use in organic chemistry is often severely limited by the high insolubility of the organic derivatives. In this review, we introduce some examples of the use of water to perform organoselenium chemistry. We mainly discuss the advantages of this medium when the recyclability is demonstrated and when the water can control the selectivity of a reaction or enhance the reaction rate.

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“The green side of the moon: ecofriendly aspects of organoselenium chemistry”

Abstract: Key aspects for the development of a greener synthesis and the use of the organoselenium compounds.

Cited by 176 publications

References 153 publications

Contrasting Reactivity of 2‐chloro‐1‐formyl‐3‐hydroxymethylenecyclohexene and its Schiff Bases towards Disodium Diselenide: Isolation of Selenospirocycles versus Azapentalenes

Contrasting Reactivity of 2‐chloro‐1‐formyl‐3‐hydroxymethylenecyclohexene and its Schiff Bases towards Disodium Diselenide: Isolation of Selenospirocycles versus Azapentalenes

Reaction of Acyl Chlorides withIn SituFormed Zinc Selenolates: Synthesis of SelenoestersversusRing-Opening Reaction of Tetrahydrofuran

Water and Aqueous Mixtures as Convenient Alternative Media for Organoselenium Chemistry

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