Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones

Sebastian Armin Schwengers; Gabriela Guillermina Gerosa; Tynchtyk Amatov; Naoki Yasukawa; Sebastian Brunen; Markus Leutzsch; Benjamin Mitschke; Grigory André Shevchenko; Benjamin List

doi:10.1002/anie.202307081

Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones

Sebastian Armin Schwengers, Gabriela Guillermina Gerosa, Tynchtyk Amatov, Naoki Yasukawa, Sebastian Brunen, Markus Leutzsch, Benjamin Mitschke, Grigory André Shevchenko, Benjamin List

Chemistry

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

Abstract

We disclose a highly regioselective, catalytic one-step dehydrogenation of α-substituted cyclic ketones in the presence of 2,3-dichlorobenzo-5,6-dicyano-1,4-benzoquinone (DDQ). The high regioselectivity originates from a phosphoric acid-catalyzed enolization, selectively affording the thermodynamically preferred enol, followed by the subsequent oxidation event. Our method provides reliable access to several α-aryl and α-alkyl substituted α,β-unsaturated ketones.

Original language	English (US)
Article number	e202307081
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	35
DOIs	https://doi.org/10.1002/anie.202307081
State	Published - Aug 28 2023

Keywords

DDQ
Enol-Catalysis
Oxidations
Phosphoric Acids
α,β-Unsaturated Ketones

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.202307081

Cite this

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title = "Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones",

abstract = "We disclose a highly regioselective, catalytic one-step dehydrogenation of α-substituted cyclic ketones in the presence of 2,3-dichlorobenzo-5,6-dicyano-1,4-benzoquinone (DDQ). The high regioselectivity originates from a phosphoric acid-catalyzed enolization, selectively affording the thermodynamically preferred enol, followed by the subsequent oxidation event. Our method provides reliable access to several α-aryl and α-alkyl substituted α,β-unsaturated ketones.",

keywords = "DDQ, Enol-Catalysis, Oxidations, Phosphoric Acids, α,β-Unsaturated Ketones",

author = "Schwengers, {Sebastian Armin} and Gerosa, {Gabriela Guillermina} and Tynchtyk Amatov and Naoki Yasukawa and Sebastian Brunen and Markus Leutzsch and Benjamin Mitschke and Shevchenko, {Grigory Andr{\'e}} and Benjamin List",

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doi = "10.1002/anie.202307081",

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T1 - Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones

AU - Schwengers, Sebastian Armin

AU - Gerosa, Gabriela Guillermina

AU - Amatov, Tynchtyk

AU - Yasukawa, Naoki

AU - Brunen, Sebastian

AU - Leutzsch, Markus

AU - Mitschke, Benjamin

AU - Shevchenko, Grigory André

AU - List, Benjamin

PY - 2023/8/28

Y1 - 2023/8/28

N2 - We disclose a highly regioselective, catalytic one-step dehydrogenation of α-substituted cyclic ketones in the presence of 2,3-dichlorobenzo-5,6-dicyano-1,4-benzoquinone (DDQ). The high regioselectivity originates from a phosphoric acid-catalyzed enolization, selectively affording the thermodynamically preferred enol, followed by the subsequent oxidation event. Our method provides reliable access to several α-aryl and α-alkyl substituted α,β-unsaturated ketones.

AB - We disclose a highly regioselective, catalytic one-step dehydrogenation of α-substituted cyclic ketones in the presence of 2,3-dichlorobenzo-5,6-dicyano-1,4-benzoquinone (DDQ). The high regioselectivity originates from a phosphoric acid-catalyzed enolization, selectively affording the thermodynamically preferred enol, followed by the subsequent oxidation event. Our method provides reliable access to several α-aryl and α-alkyl substituted α,β-unsaturated ketones.

KW - DDQ

KW - Enol-Catalysis

KW - Oxidations

KW - Phosphoric Acids

KW - α,β-Unsaturated Ketones

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DO - 10.1002/anie.202307081

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SN - 1433-7851

VL - 62

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 35

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ER -

Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones

Abstract

Keywords

ASJC Scopus subject areas

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