α-N-Heteroarylation and α-Azidation of Ketones via Enolonium Species

Atul A. More; Gulab K. Pathe; Keshaba N. Parida; Shimon Maksymenko; Yuriy B. Lipisa; Alex M. Szpilman

doi:10.1021/acs.joc.7b03058

α-N-Heteroarylation and α-Azidation of Ketones via Enolonium Species

Atul A. More
, Gulab K. Pathe
, Keshaba N. Parida
, Shimon Maksymenko
, Yuriy B. Lipisa
, Alex M. Szpilman

Department of Chemical Sciences

Research output: Contribution to journal › Article › peer-review

43 Scopus citations

Abstract

Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.

Original language	English
Pages (from-to)	2442-2447
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	83
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.7b03058
State	Published - 16 Feb 2018

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abstract = "Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.",

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AU - More, Atul A.

AU - Pathe, Gulab K.

AU - Parida, Keshaba N.

AU - Maksymenko, Shimon

AU - Lipisa, Yuriy B.

AU - Szpilman, Alex M.

PY - 2018/2/16

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N2 - Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.

AB - Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.

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α-N-Heteroarylation and α-Azidation of Ketones via Enolonium Species

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