In situ generation of the Ohira-Bestmann Reagent from stable sulfonyl azide: scalable synthesis of alkynes from aldehydes

Tue Heesgaard Jepsen; Jesper Langgaard Kristensen

doi:10.1021/jo501803f

In situ generation of the Ohira-Bestmann Reagent from stable sulfonyl azide: scalable synthesis of alkynes from aldehydes

Tue Heesgaard Jepsen, Jesper Langgaard Kristensen

23 Citations (Scopus)

Abstract

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

Original language	English
Journal	Journal of Organic Chemistry
Volume	79
Issue number	19
Pages (from-to)	9423-9426
Number of pages	4
ISSN	0022-3263
DOIs	https://doi.org/10.1021/jo501803f
Publication status	Published - 3 Oct 2014

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title = "In situ generation of the Ohira-Bestmann Reagent from stable sulfonyl azide: scalable synthesis of alkynes from aldehydes",

abstract = "We report an improved method for in situ generation of the Ohira-Bestmann reagent. Using the recently reported bench-stable imidazole-1-sulfonyl azide as diazotransfer reagent, this new method represents a scalable and convenient approach for the transformation of aldehydes into terminal alkynes. The method features an easier workup compared to the existing in situ protocol due to increased aqueous solubility of waste products.",

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

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DO - 10.1021/jo501803f

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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In situ generation of the Ohira-Bestmann Reagent from stable sulfonyl azide: scalable synthesis of alkynes from aldehydes

Abstract

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