Synthesis of 2,3-Disubstituted Benzo[<i>b</i>]selenophenes via Electrophilic Cyclization

Kesharwani, Tanay; Worlikar, Shilpa A.; Larock, Richard C.

doi:10.1021/jo0524268

Cited by 144 publications

(69 citation statements)

References 54 publications

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“…Recently, Larock and co-workers reported that 2,3-disubsti- [17] Inspired by Larock's reaction, we extended this method to access new fused chalcogenophenes 4a-e. Gratifyingly, we found that the electrophilic cyclization of 3-alkynyldihydroselenophenes with I 2 in CH 2 Cl 2 as the solvent at room temperature afforded the desired fused chalcogenophenes 4a-e in moderated to good yields (Table 3).…”

Section: Resultsmentioning

confidence: 99%

“…This methodology takes advantage, in most cases, by the presence of a halogen atom suitable to suffer further transformations. This cyclization has been used as an efficient tool in the synthesis of highly substituted indoles, [11] furans, [12] thiophenes, [13] selenophenes, [14] benzo[b]furans, [15] benzo [b]thiophenes, [16] benzo [b]selenophenes, [17] lactones, [18] and pyrroles [19] by employing electrophiles like I 2 , ICl, or chalcogen derivatives. [20] These and especially the knowledge that 3-alkynyldihydroselenophenes are promising candidates for electrophilic cyclization reactions to form fused selenophenes prompted us to develop a complete investigation on the synthesis of 3-alkynyldihydroselenophenes from 3-iododihydroselenophenes as the sequence showed in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Reactivity of 3‐Alkynyldihydroselenophene Derivatives

Rosário¹,

Schumacher²,

Gay³

et al. 2010

Eur J Org Chem

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We present herein our results on the synthesis of 3-alkynyldihydroselenophenes by palladium-catalyzed Sonogashira cross-coupling of 3-iododihydroselenophenes with different alkynes under mild conditions in good to excellent yields. The developed protocol tolerated a wide range of functional groups in the dihydroselenophenes and alkynes. These 3-alkynyldihydroselenophenes, bearing the chalcogen group,

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactivity of 3‐Alkynyldihydroselenophene Derivatives

Rosário¹,

Schumacher²,

Gay³

et al. 2010

Eur J Org Chem

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“… a Reaction Condition A: All reactions were performed using 0.30 mmol of the alkyne, 5 equiv of NaX, and 5 equiv of CuSO 4 •5H 2 O in 5 mL of EtOH at room temperature for 24 h. b Isolated yields. c Literature yield via halocyclization. d reference 23b. e reference 24. f reference 26 …”

Section: Figurementioning

confidence: 99%

“…26 Herein we disclose the first ever report of this chlorocyclization reaction starting with 2-alkynylmethylselenobenzene 12 using table salt and the green solvent ethanol (Table 1, entry 10). The resulting 3-chlorobenzo[ b ]selenophene 22 was obtained in a good yield of 72%.…”

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confidence: 96%

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Green synthesis of halogenated thiophenes, selenophenes and benzo[b]selenophenes using sodium halides as a source of electrophilic halogens

Kesharwani

Giraudy

Morgan

et al. 2017

Tetrahedron Letters

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Herein, we report the first synthesis of chlorinated benzo[b]selenophenes via environmentally friendly electrophilic chlorocyclization reaction using “table salt” as a source of “electrophilic chlorine” and ethanol as a solvent. In addition, the synthesis of diverse halogenated heterocycles, including 3-chloro, 3-bromo and 3-iodo thiophenes, selenophenes, and benzo[b]selenophenes was successfully accomplished under the same environmentally benign reaction conditions. This methodology has several advantages over other previously reported reactions as it employs simple starting compounds, an environmentally friendly solvent, ethanol, and non-toxic inorganic reagents under mild reaction conditions, resulting in the high product yields.

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Synthesis of Organoselenium Compounds

Zade

Singh

2012

Patai's Chemistry of Functional Groups

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In this chapter the major advances in the synthetic methodology and the syntheses of novel organoselenium compounds‐since 1987 are reviewed. These are presented in the order of oxidation states i.e. in the initial parts of the chapter developments in the area of the synthesis of low valent organoselenium compounds are discussed. These include: diselenides, selenides, selenols, selenolesters, selenones, selenocyanate, selenenyl halides and related derivatives. The latter part of the chapter deals with the syntheses of high valent i.e. selenium (IV) and selenium (VI) compounds. Diselenides are generally prepared by the reaction of alkali metal chalcogenolates with appropriate organic halides. There has been a lot of activity in the area of the synthesis of selenides. The procedures include: epoxide ring opening, aziridine and other ring opening, addition to double and triple bonds, transition metal and Main Group Element catalyzed coupling reactions, nucleophilic substitution reactions, etc. The novel compounds described include: selenocystine derivatives, chiral diselenides, triselenides, oranoselenenyl cations, selenium‐containing pincer ligands for catalysis, selenols and nitrososelenol derivatives, selenenyl azides. The chapter is based on over 350 original references.

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Synthesis of 2,3-Disubstituted Benzo[b]selenophenes via Electrophilic Cyclization

Cited by 144 publications

References 54 publications

Synthesis and Reactivity of 3‐Alkynyldihydroselenophene Derivatives

Synthesis and Reactivity of 3‐Alkynyldihydroselenophene Derivatives

Green synthesis of halogenated thiophenes, selenophenes and benzo[b]selenophenes using sodium halides as a source of electrophilic halogens

Synthesis of Organoselenium Compounds

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