Pt(IV)-catalyzed cyclization of arene-alkyne substrates via C-H bond functionalization |
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Authors: | Stefan J PastineSo Won Youn Dalibor Sames |
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Affiliation: | Department of Chemistry, Columbia University, 3000 Broadway MC 3167, New York, NY 10027, USA |
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Abstract: | We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. |
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Keywords: | C-H fuctionalization C-H activation platinum(IV) hydroarylation alkynes chromenes benzopyrans |
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