Premium
Synthesis and Utilization of Nitroalkyne Equivalents in Batch and Continuous Flow
Author(s) -
Morse Peter D.,
Jamison Timothy F.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706157
Subject(s) - chemistry , cycloaddition , continuous flow , yield (engineering) , combinatorial chemistry , alkyl , reactivity (psychology) , flow chemistry , aryl , nitro , sequence (biology) , reaction conditions , organic chemistry , catalysis , materials science , biochemical engineering , medicine , biochemistry , alternative medicine , pathology , engineering , metallurgy
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.