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Synfacts 2010(7): 0811-0811
DOI: 10.1055/s-0029-1220047
DOI: 10.1055/s-0029-1220047
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium-Catalyzed Oxidative Arylation of ortho-Phenylcarbamates with Arenes
Contributor(s):Paul Knochel, Tobias ThalerX. Zhao, C. S. Yeung, V. M. Dong*
University of Toronto, Canada
Palladium-Catalyzed ortho-Arylation of o-Phenylcarbamates with Simple Arenes and Sodium Persulfate
J. Am. Chem. Soc. 2010, 132: 5837-5844
University of Toronto, Canada
Palladium-Catalyzed ortho-Arylation of o-Phenylcarbamates with Simple Arenes and Sodium Persulfate
J. Am. Chem. Soc. 2010, 132: 5837-5844
Further Information
Publication History
Publication Date:
22 June 2010 (online)
Key words
ortho-arylation - C-H activation - C-H functionalization - palladium
Significance
A highly useful method for the oxidative palladium-catalyzed coupling of simple arenes and ortho-phenylcarbamates was developed. The reaction proceeds via double C-H bond functionalization with high regioselectivities including electron-rich, -neutral, and -deficient arenes as substrates.
Comment
This novel coupling method enables a most straightforward access to biaryls form simple arenes solely via C-H functionalization. Inexpensive and environmentally benign sodium persulfate (Na2S2O8) is used as oxidant. The mechanism proposed for this reaction is supported by the X-ray structure of the palladacycle P.