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Suzuki H, Igarashi R, Yamashita Y, et al. Catalytic Direct-type 1,4-Addition Reactions of Alkylazaarenes. Angew Chem Int Ed Engl. 2017;56(16):4520-4524doi: 10.1002/anie.201611374.
Suzuki, H., Igarashi, R., Yamashita, Y., & Kobayashi, S. (2017). Catalytic Direct-type 1,4-Addition Reactions of Alkylazaarenes. Angewandte Chemie (International ed. in English), 56(16), 4520-4524. https://doi.org/10.1002/anie.201611374
Suzuki, Hirotsugu, et al. "Catalytic Direct-type 1,4-Addition Reactions of Alkylazaarenes." Angewandte Chemie (International ed. in English) vol. 56,16 (2017): 4520-4524. doi: https://doi.org/10.1002/anie.201611374
Suzuki H, Igarashi R, Yamashita Y, Kobayashi S. Catalytic Direct-type 1,4-Addition Reactions of Alkylazaarenes. Angew Chem Int Ed Engl. 2017 Apr 10;56(16):4520-4524. doi: 10.1002/anie.201611374. Epub 2017 Mar 20. PMID: 28318086.
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Angew Chem Int Ed Engl. 2017 Apr 10;56(16):4520-4524. doi: 10.1002/anie.201611374. Epub 2017 Mar 20.

Catalytic Direct-type 1,4-Addition Reactions of Alkylazaarenes.

Angewandte Chemie (International ed. in English)

Hirotsugu Suzuki, Ryo Igarashi, Yasuhiro Yamashita, Shū Kobayashi

Affiliations

  1. Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, Japan.

PMID: 28318086 DOI: 10.1002/anie.201611374

Abstract

1,4-addition reactions of alkylazaarenes catalyzed by strong Brønsted bases have been developed for the first time. The desired reactions with α,β-unsaturated amides proceeded under mild reaction conditions to give the 1,4-adducts in high yields. Both ortho- and para-substituted azaarenes afforded the desired adducts in high yields. Regioselective reactions of di- or trimethylpyridine were found to be possible depending on the acidity of the α-hydrogen atoms. Furthermore, a candidate of allosteric protein kinase modulators was synthesized in two steps. An asymmetric variant of this reaction was also found to be feasible.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: 1,4-addition; Brønsted bases; anions; arenes; crown compounds

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