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:https://doi.org/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

Ariel University

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

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

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Transition-Metal-Free Intermolecular α-Arylation of Ketones via Enolonium Species",

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.",

author = "Shimon Maksymenko and Parida, {Keshaba N.} and Pathe, {Gulab K.} and More, {Atul A.} and Lipisa, {Yuriy B.} and Szpilman, {Alex M.}",

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doi = "https://doi.org/10.1021/acs.orglett.7b03064",

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T1 - Transition-Metal-Free Intermolecular α-Arylation of Ketones via Enolonium Species

AU - Maksymenko, Shimon

AU - Parida, Keshaba N.

AU - Pathe, Gulab K.

AU - More, Atul A.

AU - Lipisa, Yuriy B.

AU - Szpilman, Alex M.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - 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.

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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DO - https://doi.org/10.1021/acs.orglett.7b03064

M3 - مقالة

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SN - 1523-7060

VL - 19

SP - 6312

EP - 6315

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

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

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