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Synfacts 2015; 11(3): 0241
DOI: 10.1055/s-0034-1380234
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Synthesis of Isatins from Anilines by Double Carbonylation

Contributor(s):
Victor Snieckus
,
M. Selim Hossain (Snieckus Innovations)
Li W, Duan Z, Zhang X, Zhang H, Wang M, Jiang R, Zeng H, Liu C, Lei A * Wuhan University, Lanzhou Institute of Chemical Physics, and Leshan Normal University, P. R. of China
From Anilines to Isatins: Oxidative Palladium-Catalyzed Double Carbonylation of C–H Bonds.

Angew. Chem. Int. Ed. 2015;
54: 1893-1896
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Publication History

Publication Date:
16 February 2015 (online)

 
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Key words

isatins - palladium catalysis - carbonylation - anilines

Significance

Lei and co-workers report a palladium-catalyzed synthesis of isatins by double carbonylation and ortho C–H bond activation of aniline derivatives. Poor to good substrate scope was observed under the optimized reaction conditions. A mechanism is suggested, in which palladium C–H bond insertion is followed by the two consecutive CO insertion reactions.


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Comment

The isatin structure has been given privileged status because of the generation of a large number of structurally diverse derivatives which inhibit cancer cell proliferation and tumor growth by interaction with a variety of intracellular targets such as DNA, telomerase, tubulin, P-glycoprotein, protein kinases, and phosphatases (K. L. Vine, J. M. Locke, M. Ranson, K. Benkendorff, S. G. Pyne, J. B. Bremner Bioorg. Med. Chem. 2007, 15, 931). In the present methodology, substrates and catalysts were inadequately studied. The origin of poor yields (e.g., 1 and 2) were also unidentified.


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