Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.
In: Journal of the American Chemical Society, Jg. 140 (2018-04-18), Heft 15, S. 5300-5310
Online
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Zugriff:
A mild and operationally simple copper-catalyzed vinylogous aerobic oxidation of β,γ- and α,β-unsaturated esters is described. This method features good yields, broad substrate scope, excellent chemo- and regioselectivity, and good functional group tolerance. This method is additionally capable of oxidizing β,γ- and α,β-unsaturated aldehydes, ketones, amides, nitriles, and sulfones. Furthermore, the present catalytic system is suitable for bisvinylogous and trisvinylogous oxidation. Tetramethylguanidine (TMG) was found to be crucial in its role as a base, but we also speculate that it serves as a ligand to copper(II) triflate to produce the active copper(II) catalyst. Mechanistic experiments conducted suggest a plausible reaction pathway via an allylcopper(II) species. Finally, the breadth of scope and power of this methodology are demonstrated through its application to complex natural product substrates. [ABSTRACT FROM AUTHOR]
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Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.
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Autor/in / Beteiligte Person: | Zhang, Hai-Jun ; Schuppe, Alexander W. ; Pan, Shi-Tao ; Chen, Jin-Xiang ; Wang, Bo-Ran ; Newhouse, Timothy R. ; Yin, Liang |
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Zeitschrift: | Journal of the American Chemical Society, Jg. 140 (2018-04-18), Heft 15, S. 5300-5310 |
Veröffentlichung: | 2018 |
Medientyp: | academicJournal |
ISSN: | 0002-7863 (print) |
DOI: | 10.1021/jacs.8b01886 |
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