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  Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine

Koleda, O., Broese, T., Noetzel, J., Roemelt, M., Suna, E., & Francke, R. (2017). Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine. The Journal of Organic Chemistry, 82(22), 11669-11681. doi:10.1021/acs.joc.7b01686.

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Genre: Journal Article

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 Creators:
Koleda, Olesja1, Author
Broese, Timo2, Author
Noetzel, Jan3, Author
Roemelt, Michael3, 4, Author              
Suna, Edgars1, Author
Francke, Robert2, Author
Affiliations:
1Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia, ou_persistent22              
2Institute of Chemistry, Rostock University, Albert-Einstein-Str. 3a, 18059 Rostock, Germany, ou_persistent22              
3Lehrstuhl für Theoretische Chemie, Ruhr-University Bochum, 44780 Bochum, Germany, ou_persistent22              
4Research Group Roemelt, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_3018043              

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 Abstract: The indirect (“ex-cell”) electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our “ex-cell” approach toward the electrosynthesis of benzoxazoles is compatible with a range of redox-sensitive functional groups. An unprecedented concerted reductive elimination mechanism for benzoxazole formation is proposed on the basis of control experiments and DFT calculations.

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Language(s): eng - English
 Dates: 2017-07-052017-08-112017-11-17
 Publication Status: Published in print
 Pages: 13
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.joc.7b01686
 Degree: -

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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 82 (22) Sequence Number: - Start / End Page: 11669 - 11681 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1