Cyclization of aryl 3-aryl propynoates into 4-arylcoumarins catalyzed by cyclometalated Platinum(II) complexes

Cyclometalated (ppy)PtII complexes (ppy = 2-phenylpyridinato-C2,N) catalyze the intramolecular cyclization of aryl propynoates to form coumarins and benzocoumarins. The complex [(ppy)PtCl(MeCN)] (5 mol %) was the most active and efficient catalyst for such reaction, especially in the presence of AgS...

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Bibliographic Details
Published in:Tetrahedron 2020-04, Vol.76 (14), p.131029, Article 131029
Main Authors: Zaitceva, Olesia, Bénéteau, Valérie, Ryabukhin, Dmitry S., Eliseev, Ivan I., Kinzhalov, Mikhal A., Louis, Benoit, Vasilyev, Aleksander V., Pale, Patrick
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
Coumarin
Cyclization
Platinacycle
Platinum
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Summary:Cyclometalated (ppy)PtII complexes (ppy = 2-phenylpyridinato-C2,N) catalyze the intramolecular cyclization of aryl propynoates to form coumarins and benzocoumarins. The complex [(ppy)PtCl(MeCN)] (5 mol %) was the most active and efficient catalyst for such reaction, especially in the presence of AgSbF6 (15 mol %) in 1,2-dichloroethane. With this catalytic system, a wide range of substituents and functional groups proved compatible with the cyclization process, leading to a large variety of substituted coumarins and benzocoumarins (22 examples, 77–99%) [Display omitted] •The synthesis of dimeric and monomeric cyclometalated Platinum(II) complexes is reported.•The cyclization of aryl propynoates to coumarins and benzocoumarins is reported.•2- phenylpyridinato-C2,N)Pt(II) complexe is a very efficient catalyst for these cyclizations.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131029