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Synfacts 2013; 9(1): 0091
DOI: 10.1055/s-0032-1317729
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ruthenium-Catalyzed ortho-Arylation and Alkenylation of N-Alkyl Benzamides

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Chinnagolla RK, Jeganmohan M * Indian Institute of Science Education and Research, Pune, India
Regioselective Ortho-Arylation and Alkenylation of N-Alkyl Benzamides with Boronic Acids via Ruthenium-Catalyzed C–H Bond Activation: An Easy Route to Fluorenones Synthesis.

Org. Lett. 2012;
14: 5246-5249
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

ruthenium - boronic acids - ortho-arylation

Significance

The authors report a highly regio­selective ruthenium-catalyzed ortho-arylation and alkenylation of various N-alkyl benzamides with different (hetero)aromatic and alkenyl boronic acids in the presence of silver salts. The corresponding benzamides are obtained in good to very good yield.


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Comment

Noteworthy, this methodology may be applied to the synthesis of fluorenones by treatment of the biarylic coupling products with tri­fluoroacetic anhydride and hydrogen chloride.


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