Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters

Wanida Munbunjong; Eun Hwa Lee; Poonlarp Ngernmaneerat; Sung Jun Kim; Gurpinder Singh; Warinthorn Chavasiri; Doo Ok Jang

doi:10.1016/j.tet.2009.01.072

Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters

Wanida Munbunjong, Eun Hwa Lee, Poonlarp Ngernmaneerat, Sung Jun Kim, Gurpinder Singh, Warinthorn Chavasiri, Doo Ok Jang

Chemistry and Medical Chemistry

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

Abstract

A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.

Original language	English
Pages (from-to)	2467-2471
Number of pages	5
Journal	Tetrahedron
Volume	65
Issue number	12
DOIs	https://doi.org/10.1016/j.tet.2009.01.072
Publication status	Published - 2009 Mar 21

Bibliographical note

Funding Information:
This work was supported by the Center for Bioactive Molecular Hybrids and Yonsei University. W.M. is thankful to Thailand Research Fund for the 2004 Royal Golden Jubilee Ph.D. research assistant fellowship.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.01.072

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title = "Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters",

abstract = "A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.",

author = "Wanida Munbunjong and Lee, {Eun Hwa} and Poonlarp Ngernmaneerat and Kim, {Sung Jun} and Gurpinder Singh and Warinthorn Chavasiri and Jang, {Doo Ok}",

note = "Funding Information: This work was supported by the Center for Bioactive Molecular Hybrids and Yonsei University. W.M. is thankful to Thailand Research Fund for the 2004 Royal Golden Jubilee Ph.D. research assistant fellowship.",

year = "2009",

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doi = "10.1016/j.tet.2009.01.072",

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T1 - Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide

T2 - efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters

AU - Munbunjong, Wanida

AU - Lee, Eun Hwa

AU - Ngernmaneerat, Poonlarp

AU - Kim, Sung Jun

AU - Singh, Gurpinder

AU - Chavasiri, Warinthorn

AU - Jang, Doo Ok

N1 - Funding Information: This work was supported by the Center for Bioactive Molecular Hybrids and Yonsei University. W.M. is thankful to Thailand Research Fund for the 2004 Royal Golden Jubilee Ph.D. research assistant fellowship.

PY - 2009/3/21

Y1 - 2009/3/21

N2 - A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.

AB - A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.

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JF - Tetrahedron

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Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters

Abstract

Bibliographical note

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