Synthesis and Utilization of Nitroalkyne Equivalents in Batch and Continuous Flow
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Morse_et_al-2017-Angewandte_Chemie_International_Edition.pdf
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1.67 MB
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Author(s)
Morse, Peter D
Jamison, Timothy F
Date Issued
October 2017
Journal
Angewandte Chemie International Edition
Publisher
Wiley Blackwell
Citation
Morse, Peter D., and Jamison, Timothy F. “Synthesis and Utilization of Nitroalkyne Equivalents in Batch and Continuous Flow.” Angewandte Chemie International Edition 56, 45 (October 2017): 13999–14002 © 2017 Wiley-VCH Verlag GmbH & Co
Version
Final published version
Abstract
We report a method for overcoming the low stability of nitroalkynes through the development of nitrated vinyl silyltriflate equivalents. Because of their instability, nitroalkynes have only rarely been utilized in synthesis. The reactivity of these silyltriflates, which are prepared in situ, is exemplified by dipolar cycloaddition reactions with nitrones to give highly substituted 4-nitro-4-isoxazolines in high yields. This approach has proven general for several different alkyl and aryl substituted alkynes. In order to minimize the accumulation of potentially hazardous reaction intermediates, we have also developed a continuous flow variant of this method that is capable of carrying out the entire reaction sequence in a good yield and a short residence time.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution 4.0 International License
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DOI of Published Version
https://doi.org/10.1002/anie.201706157
