Synthesis of 2‐Organylchalcogenyl–benzo[b]selenophenes: 1‐(2,2‐Dibromovinyl)‐2‐butylselenanylbenzenes as Precursors to Access Alkynes Susceptible to Cyclization

A convenient synthesis of 1‐(2‐organylchalcogenylethynyl)‐2‐butylselenanylbenzenes was established taking advantage of the selective reaction of 1‐(2,2‐dibromovinyl)‐2‐butylselenanylbenzenes with thiols or diorganyl diselenides. The new 1‐(2‐chalcogenylethynyl)‐2‐butylselenanylbenzenes were prepared...

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Veröffentlicht in:ChemistrySelect (Weinheim) 2017-05, Vol.2 (16), p.4561-4566
Hauptverfasser: Perin, Gelson, Roehrs, Juliano A., Hellwig, Paola S., Stach, Guilherme, Barcellos, Thiago, Lenardão, Eder J., Jacob, Raquel G., Luz, Eduardo Q.
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Sprache:eng
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Zusammenfassung:A convenient synthesis of 1‐(2‐organylchalcogenylethynyl)‐2‐butylselenanylbenzenes was established taking advantage of the selective reaction of 1‐(2,2‐dibromovinyl)‐2‐butylselenanylbenzenes with thiols or diorganyl diselenides. The new 1‐(2‐chalcogenylethynyl)‐2‐butylselenanylbenzenes were prepared in good yields and used as precursors of 2‐organylchalcogenylbenzo[b]selenophenes via electrophilic cyclization using I2, Br2 or PhSeBr as electrophiles. Different classes of new 3‐substituted‐ (3‐iodo, 3‐bromo, 3‐phenylselenanyl) benzo[b]selenophenes were prepared in good yields. The synthetic application of the obtained products was demonstrated employing the benzo[b]selenophenes in Suzuki and Sonogashira cross‐coupling reactions. 2‐Organylchalcogenylbenzo[b]selenophenes were prepared from 1‐(2,2‐dibromovinyl)‐2‐butylselenanylbenzenes. The corresponding precursors could be obtained in high yields and with excellent chemoselectivity. The resulting benzo[b]selenophes proved to be versatile as precursors of highly functionalized compounds.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201700948