Undecorated Cu(OAc)2-Catalyzed C(sp3)-C(sp3) Bond Formation through para-Hydroxy Group Triggered Remote Benzylic C(sp3)-H Bond Functionalization
The undecorated Cu(OAc)2‐catalyzed para‐hydroxy group triggered oxidative coupling of 2,6‐disubstituted 4‐cresols with fluorinated β‐keto esters or malonates leading to benzylic C(sp3)–C(sp3) bond formation was investigated. This formal double C(sp3)–H coupling method features mild conditions, atom...
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Veröffentlicht in: | European journal of organic chemistry 2015-08, Vol.2015 (24), p.5334-5338 |
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Sprache: | eng |
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Zusammenfassung: | The undecorated Cu(OAc)2‐catalyzed para‐hydroxy group triggered oxidative coupling of 2,6‐disubstituted 4‐cresols with fluorinated β‐keto esters or malonates leading to benzylic C(sp3)–C(sp3) bond formation was investigated. This formal double C(sp3)–H coupling method features mild conditions, atom economy, ligand‐ and additive‐free catalysis, and ambient air as the terminal oxidant. This ecofriendly method allows rapid access to highly functionalized 3‐phenylpropanoate derivatives containing fluorinated quaternary carbon‐like centers. On the basis of active p‐benzoquinone methide intermediates, a plausible mechanism was proposed.
The Cu(OAc)2‐catalyzed para‐hydroxy group triggered oxidative coupling of 2,6‐disubstituted‐4‐cresols with fluorinated β‐ketone esters or malonates leading to benzylic C(sp3)–C(sp3) bond formation is described with ambient air as the terminal oxidant. Highly functionalized 3‐phenylpropanoate derivatives containing fluorinated quaternary carbon‐like centers are constructed in an ecofriendly manner. |
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ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201500706 |