Synthesis of Unsymmetrical Pyridyl Aryl Selenides by the Reductive Cleavage of Se─Se Bond

Bhasin, K. K.; Doomra, Shivani; Kaur, Gurjeet; Arora, Ekta; Singh, Neelam; Nagpal, Yogesh; Kumar, Rajeev; Rishu,; Klapoetke, Thomas M.; Mehta, S.K.

doi:10.1080/10426500801900980

Cited by 12 publications

(2 citation statements)

References 28 publications

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“…Synthesis of heterocyclic chalcogenic molecules is a topic of great challenge among the synthetic organic community. Most reported transformations involve the nucleophilic substitution of 2‐halopyridines with salts of selenols or transition metal catalyzed cross‐coupling reactions of diselenides with aryl boronic acids (Scheme a) or 2‐halopyridines (Scheme b). In addition, Alves et al have reported the synthesis of these moieties via the reaction of 2‐halopyridines with diselenides using glycerol as solvent and hypophosphorus acid as the reducing agent (Scheme b) .…”

Section: Introductionmentioning

confidence: 99%

An Expeditious and Environmentally‐Benign Approach to 2‐Aryl/Heteroaryl Selenopyridines via Ruthenium Catalyzed [2+2+2] Cycloadditions

et al. 2019

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A highly efficient protocol for the synthesis of 2‐aryl/ hetero aryl selenopyridines has been developed via a ruthenium(II)‐catalyzed cycloaddition reaction of 1,6‐diynes with aryl/heteroaryl selenocyanates with good to excellent yields. It was found that various diynes and selenocyanates expediently underwent the reaction under open‐flask conditions. This atom‐economical catalytic strategy offers a mild and practical approach to access a variety of such cycloadducts with excellent regioselectivities.

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Section: Introductionmentioning

confidence: 99%

An Expeditious and Environmentally‐Benign Approach to 2‐Aryl/Heteroaryl Selenopyridines via Ruthenium Catalyzed [2+2+2] Cycloadditions

et al. 2019

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“…Specifically, synthetic routes for the introduction of seleno-substituents into organic molecule which are the building blocks for the synthesis of modified selenocarbohydrates, selenoaminoacids and selenoproteins have attracted much attention due to their interesting structural and biological properties [3]. Literature is inundated with several synthetic methods for the synthesis of selenide anion, the more important of which include the use of reduction of diorganyl diselenide with sodium [4], samarium diiodide [5], Sm/TMSCl [6] and catalyzed system Cu 2 O/Mg/bpy [7]. Moreover, Grignard reagents [8,9] also react with selenium to give equivalent species of selenide anions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Symmetrical and Unsymmetrical Analogues of 1,2-bis[bis(4-chlorophenyl) Methyl] Diselane

Kumar¹

2015

ujc

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The 'living' species selenide anion Se 2 2-, generated in situ by the reduction of 1,2-bis(bis(4-chlorophenyl)methyl)diselane with sodium borohydride, was treated with various organic halides to afford synthetically important organoselenium compounds including α,ω-diselenoethers and selenides bearing ester functionality, under mild and neutral conditions. These compounds have been characterized analytically with the help of various spectroscopic techniques viz., IR, multinuclear NMR (1 H, 13 C, 77 Se) and mass spectrometry.

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NMR of Organoselenium and Organotellurium Compounds

Panda

Singh

2012

Patai's Chemistry of Functional Groups

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This chapter gives a systematic account of and surveys the available data on 77 Se and 125 Te NMR spectra of organochalcogen compounds such as chacogenols, mono and dichalcogenides, chalcogenolates, tetra and hexa substituted chalcogen compounds, chalcogenyl halides, chalcogen‐containing heterocycles and macrocycles, chalcogen‐oxygen/nitrogen compounds, etc. The review is based on the literature from 1985 to 2011 and includes 780 references. The 77 Se/ 125 Te NMR spectra of organochalcogen compounds reveal expansive chemical shifts (δ Se /δ Te ) leading to sharp sensitivity of these nuclei (Se/Te) to their environment such as solvent, temperature, molecular geometry, ligand backbone, oxidation state, chelate ring size, steric strain, etc. This is well illustrated by the advantageous use of this spectroscopy in the successful determination of the solution state structure of several organochalcogen compounds. It is noted that the 125 Te and 77 Se chemical shifts of a large number of structurally similar organotellurium and selenium compounds show linear relationship.

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Synthesis of Unsymmetrical Pyridyl Aryl Selenides by the Reductive Cleavage of Se─Se Bond

Cited by 12 publications

References 28 publications

An Expeditious and Environmentally‐Benign Approach to 2‐Aryl/Heteroaryl Selenopyridines via Ruthenium Catalyzed [2+2+2] Cycloadditions

An Expeditious and Environmentally‐Benign Approach to 2‐Aryl/Heteroaryl Selenopyridines via Ruthenium Catalyzed [2+2+2] Cycloadditions

Synthesis and Characterization of Symmetrical and Unsymmetrical Analogues of 1,2-bis[bis(4-chlorophenyl) Methyl] Diselane

NMR of Organoselenium and Organotellurium Compounds

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