α-Arylation of Carbonyl Compounds through Oxidative C−C Bond Activation

Jing Li; Adriano Bauer; Giovanni Di Mauro; Nuno Maulide

doi:10.1002/anie.201904899

α-Arylation of Carbonyl Compounds through Oxidative C−C Bond Activation

Jing Li, Adriano Bauer, Giovanni Di Mauro, Nuno Maulide

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

28 Citations (Scopus)

Abstract

A synthetically useful approach for the direct α-arylation of carbonyl compounds through a novel oxidative C−C bond activation is reported. This mechanistically unusual process relies on a 1,2-aryl shift and results in all-carbon quaternary centers. The transformation displays broad functional-group tolerance and can in principle also be applied as an asymmetric variant.

Original language	English
Pages (from-to)	9816-9819
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	29
DOIs	https://doi.org/10.1002/anie.201904899
Publication status	Published - 2019 Jul 15
Externally published	Yes

Keywords

C−C bond activation
arylation
enolonium species
ketones
umpolung

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201904899

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title = "α-Arylation of Carbonyl Compounds through Oxidative C−C Bond Activation",

abstract = "A synthetically useful approach for the direct α-arylation of carbonyl compounds through a novel oxidative C−C bond activation is reported. This mechanistically unusual process relies on a 1,2-aryl shift and results in all-carbon quaternary centers. The transformation displays broad functional-group tolerance and can in principle also be applied as an asymmetric variant.",

keywords = "C−C bond activation, arylation, enolonium species, ketones, umpolung",

author = "Jing Li and Adriano Bauer and {Di Mauro}, Giovanni and Nuno Maulide",

note = "Funding Information: Generous support of our research programs by the University of Vienna is acknowledged. We are grateful for financial support of this research by the ERC (CoG VINCAT), the FWF (Project P30226). Publisher Copyright: {\textcopyright} 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.",

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T1 - α-Arylation of Carbonyl Compounds through Oxidative C−C Bond Activation

AU - Li, Jing

AU - Bauer, Adriano

AU - Di Mauro, Giovanni

AU - Maulide, Nuno

N1 - Funding Information: Generous support of our research programs by the University of Vienna is acknowledged. We are grateful for financial support of this research by the ERC (CoG VINCAT), the FWF (Project P30226). Publisher Copyright: © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

PY - 2019/7/15

Y1 - 2019/7/15

N2 - A synthetically useful approach for the direct α-arylation of carbonyl compounds through a novel oxidative C−C bond activation is reported. This mechanistically unusual process relies on a 1,2-aryl shift and results in all-carbon quaternary centers. The transformation displays broad functional-group tolerance and can in principle also be applied as an asymmetric variant.

AB - A synthetically useful approach for the direct α-arylation of carbonyl compounds through a novel oxidative C−C bond activation is reported. This mechanistically unusual process relies on a 1,2-aryl shift and results in all-carbon quaternary centers. The transformation displays broad functional-group tolerance and can in principle also be applied as an asymmetric variant.

KW - C−C bond activation

KW - arylation

KW - enolonium species

KW - ketones

KW - umpolung

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JO - Angewandte Chemie - International Edition

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ER -

α-Arylation of Carbonyl Compounds through Oxidative C−C Bond Activation

Abstract

Keywords

ASJC Scopus subject areas

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