Bismuth‐Mediated α‐Arylation of Acidic Diketones with ortho ‐Substituted Boronic Acids
Abstract: The α‐arylation of cyclic and fluoroalkyl 1,3‐diketones is made challenging by the highly stabilized nature of the corresponding enolates, and is especially difficult for sterically demanding aryl partners. As a general solution to this problem, we report the Bi‐mediated oxidative coupling of acidic diones and ortho‐substituted arylboronic acids. Starting from a bench‐stable bismacycle precursor, a sequence of B‐to‐Bi transmetallation, oxidation and C−C bond formation furnishes the arylated diones. Development of methodology that tolerates both sensitive functionality and steric demand is supported by interrogation of key reactive intermediates. Application of our strategy to cyclic diones enables the concise synthesis of important agrochemical intermediates which were previously prepared using toxic Pb reagents. This methodology also enables the first ever arylation of fluoroalkyl diones which, upon condensation with hydrazine, provides direct access to valuable fluoroalkyl pyrazoles.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Bismuth‐Mediated α‐Arylation of Acidic Diketones with ortho ‐Substituted Boronic Acids ; day:29 ; month:08 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (29.08.2022) (gesamt 1)
- Urheber
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Ruffell, Katie
Argent, Stephen P.
Ling, Kenneth B.
Ball, Liam T.
- DOI
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10.1002/anie.202210840
- URN
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urn:nbn:de:101:1-2022083015485296994173
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:38 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Ruffell, Katie
- Argent, Stephen P.
- Ling, Kenneth B.
- Ball, Liam T.
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