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In Situ Generation of the Ohira-Bestmann Reagent from Stable Sulfonyl Azide: Scalable Synthesis of Alkynes from Aldehydes

Tue Heesgaard Jepsen and Jesper Langgaard Kristensen*

*Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark, Email:

T. H. Jepsen, J. L. Kristensen, J. Org. Chem., 2014, 79, 9423-9426.

DOI: 10.1021/jo501803f (free Supporting Information)


The use of the recently reported bench-stable imidazole-1-sulfonyl azide as diazotransfer reagent enables an improved method for the in situ generation of the Ohira-Bestmann reagent. This method represents a scalable and convenient approach for the transformation of aldehydes into terminal alkynes and offers an easier workup compared to the existing in situ protocol due to increased aqueous solubility of waste products.

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Key Words

Seyferth-Gilbert Homologation

ID: J42-Y2014