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Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
Author(s) -
Harenberg Johannes H.,
Weidmann Niels,
Karaghiosoff Konstantin,
Knochel Paul
Publication year - 2021
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.202012085
Subject(s) - chemistry , electrophile , lithium diisopropylamide , hexane , allylic rearrangement , medicinal chemistry , sodium , organic chemistry , continuous flow , catalysis , physics , mechanics , ion , deprotonation
The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set‐up using NaDA (sodium diisopropylamide) in EtNMe 2 or NaTMP (sodium 2,2,6,6‐tetramethylpiperidide)⋅TMEDA in n‐hexane provides sodiated acrylonitriles and alkenyl sulfides, which are subsequently trapped in batch with various electrophiles such as aldehydes, ketones, disulfides and allylic bromides affording functionalized acrylonitriles and alkenyl sulfides. This flow‐procedure was successfully extended to other acrylates by using Barbier‐type conditions.