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Issue 14, 2017
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Pd/Cu-Catalyzed tandem head-to-tail dimerization/cycloisomerization of terminal ynamides for the synthesis of 5-vinyloxazolones

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Abstract

An attractive and novel methodology involving Pd/Cu-catalyzed tandem head-to-tail dimerization/cycloisomerization of terminal ynamides for the synthesis of 3,5-disubstituted oxazolones was developed. Under Pd(PPh3)2Cl2/CuI cooperative catalyzed reaction conditions, it provided efficient access to 5-vinyloxazolones with exceptional functional group tolerance and good chemoselectivity. The control experiments demonstrated that Pd(PPh3)2Cl2 serves a key role in the dimerization of terminal ynamides and shows low catalytic activity in the intramolecular cyclization. Moreover, the hetero-Diels–Alder reaction of product 5-vinyloxazolones was also described, which provided polycyclic oxazolones in good yield.

Graphical abstract: Pd/Cu-Catalyzed tandem head-to-tail dimerization/cycloisomerization of terminal ynamides for the synthesis of 5-vinyloxazolones

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Publication details

The article was received on 16 Feb 2017, accepted on 07 Mar 2017 and first published on 07 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00381A
Citation: Org. Biomol. Chem., 2017,15, 2923-2930
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    Pd/Cu-Catalyzed tandem head-to-tail dimerization/cycloisomerization of terminal ynamides for the synthesis of 5-vinyloxazolones

    L. Tang, H. Huang, Y. Xi, G. He and H. Zhu, Org. Biomol. Chem., 2017, 15, 2923
    DOI: 10.1039/C7OB00381A

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