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

Authors
  • Jepsen, Tue Heesgaard
  • Kristensen, Jesper Langgaard
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Oct 03, 2014
Volume
79
Issue
19
Pages
9423–9426
Identifiers
DOI: 10.1021/jo501803f
PMID: 25215450
Source
Medline
License
Unknown

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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