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  The Direct Conversion of alpha-Hydroxyketones to Alkynes

Ghiringhelli, F., Nattmann, L., Bognar, S., & van Gemmeren, M. (2019). The Direct Conversion of alpha-Hydroxyketones to Alkynes. The Journal of Organic Chemistry, 84(2), 983-993. doi:10.1021/acs.joc.8b02941.

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 Creators:
Ghiringhelli, Francesca, Author
Nattmann, Lukas, Author
Bognar, Sabine, Author
van Gemmeren, Manuel1, Author           
Affiliations:
1Research Department Schlögl, Max Planck Institute for Chemical Energy Conversion, Max Planck Society, ou_3023874              

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 Abstract: Alkynes are highly important functional groups in organic chemistry, both as part of target structures and as versatile synthetic intermediates. In this study, a protocol for the direct conversion of alpha-hydroxyketones to alkynes is reported. In combination with the variety of synthetic methods that generate the required starting materials by forming the central C-C bond, it enables a highly versatile fragment coupling approach toward alkynes. A broad scope for this novel transformation is shown alongside mechanistic insights. Furthermore, the utility of our protocol is demonstrated through its application in concert with varied alpha-hydroxyketone syntheses, giving access to a broad spectrum of alkynes.

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Language(s): eng - English
 Dates: 2019
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: 000456632800049
DOI: 10.1021/acs.joc.8b02941
 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: 84 (2) Sequence Number: - Start / End Page: 983 - 993 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1