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Journal Article

The Direct Conversion of alpha-Hydroxyketones to Alkynes


van Gemmeren,  Manuel
Research Department Schlögl, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;

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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.

Cite as: https://hdl.handle.net/21.11116/0000-0005-DB71-5
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.