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BF 3 ·SMe 2 for Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles
Author(s) -
Söderström Marcus,
Zamaratski Edouard,
Odell Luke R.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900503
Subject(s) - chemistry , pyridazine , pyrazine , reagent , tandem , combinatorial chemistry , thiazole , pyrimidine , lewis acids and bases , solvent , organic chemistry , medicinal chemistry , stereochemistry , catalysis , materials science , composite material
Herein, a general, solvent‐free and straightforward thiomethylation of electron deficient heterocycles using BF 3 · SMe 2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF 3 · SMe 2 towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non‐malodorous reagent while the discovery of novel chemical transformations using BF 3 · SMe 2 provides fundamental new insights into the reactivity of this commonly employed reagent.