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

Paul Knochel; Nadja M. Barl

doi:10.1055/s-0032-1317729

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Synfacts 2013; 9(1): 0091
DOI: 10.1055/s-0032-1317729

Metal-Mediated Synthesis

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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Further Information

Publication History

Publication Date:
17 December 2012 (online)

Abstract
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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.

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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