Copper-Catalyzed C–N Cross-Coupling of Substituted 2-Halobenzoates with Secondary Acyclic Amides

Man-Gang Wang; Hua Yu; Jun Wu; Zhi-Cai Shang

doi:10.1055/s-0033-1338800

Synthesis, Table of Contents

Synthesis 2013; 45(14): 1955-1964
DOI: 10.1055/s-0033-1338800

paper

Copper-Catalyzed C–N Cross-Coupling of Substituted 2-Halobenzoates with Secondary Acyclic Amides

Man-Gang Wang

Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China Fax: +86(571)87951895 Email: shangzc@zju.edu.cn

,

Hua Yu

Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China Fax: +86(571)87951895 Email: shangzc@zju.edu.cn

,

Jun Wu*

Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China Fax: +86(571)87951895 Email: shangzc@zju.edu.cn

,

Zhi-Cai Shang*

Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China Fax: +86(571)87951895 Email: shangzc@zju.edu.cn

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Abstract

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Abstract

The copper-catalyzed C–N cross-coupling of poorly nucleophilic acyclic secondary amides with sterically hindered substituted 2-halobenzoates has been demonstrated with 1,4-dimethyl-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one (DMBDO) as ligands for the first time. The protocol is effective for the synthesis of hindered tertiary amides. We also found that the alkoxycarbonyl (CO₂R) group has a strong ortho-substituent effect on a Goldberg-type C–N coupling reaction.

Key words

copper - N-arylation - cross-coupling - amides - halobenzoates

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References

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Supporting Information

Primary Data

Primary Data