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Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates.

ABSTRACT: The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set-up using NaDA (sodium diisopropylamide) in EtNMe₂ 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.

SUBMITTER: Harenberg JH

PROVIDER: S-EPMC7821005 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates.

Harenberg Johannes H JH Weidmann Niels N Karaghiosoff Konstantin K Knochel Paul P

Angewandte Chemie (International ed. in English) 20201103 2

The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set-up using NaDA (sodium diisopropylamide) in EtNMe<sub>2</sub> 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 ex ...[more]

PMID: 33026681

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