Transition-Metal-Free Intermolecular α-Arylation of Ketones via Enolonium Species

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

doi:10.1021/acs.orglett.7b03064

Transition-Metal-Free Intermolecular α-Arylation of Ketones via Enolonium Species

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

Department of Chemical Sciences

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

47 Scopus citations

Abstract

Herein it is shown, for the first time, that enolonium species are powerful electrophiles capable of reacting with aromatic compounds in an intermolecular manner to afford α-arylated ketones. The reaction is compatible with a variety of functional groups, is of wide scope with respect to aromatic compounds and ketone, and even works for polymerization-prone substrates such as substituted pyrroles, thiophenes, and furans. Only 1.6 to 5 equiv of the commodity aromatic substrates is needed.

Original language	English
Pages (from-to)	6312-6315
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.7b03064
State	Published - 1 Dec 2017

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abstract = "Herein it is shown, for the first time, that enolonium species are powerful electrophiles capable of reacting with aromatic compounds in an intermolecular manner to afford α-arylated ketones. The reaction is compatible with a variety of functional groups, is of wide scope with respect to aromatic compounds and ketone, and even works for polymerization-prone substrates such as substituted pyrroles, thiophenes, and furans. Only 1.6 to 5 equiv of the commodity aromatic substrates is needed.",

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AU - Parida, Keshaba N.

AU - Pathe, Gulab K.

AU - More, Atul A.

AU - Lipisa, Yuriy B.

AU - Szpilman, Alex M.

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AB - Herein it is shown, for the first time, that enolonium species are powerful electrophiles capable of reacting with aromatic compounds in an intermolecular manner to afford α-arylated ketones. The reaction is compatible with a variety of functional groups, is of wide scope with respect to aromatic compounds and ketone, and even works for polymerization-prone substrates such as substituted pyrroles, thiophenes, and furans. Only 1.6 to 5 equiv of the commodity aromatic substrates is needed.

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Transition-Metal-Free Intermolecular α-Arylation of Ketones via Enolonium Species

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