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Zwitterion-Catalyzed Deacylative Dihalogenation of β-Oxo Amides

Zhihai Ke*, Ying-Pong Lam, Kin-San Chan and Ying-Yeung Yeung*

*Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, Email: chmkzcuhk.edu.hk, yyyeungcuhk.edu.hk

Z. Ke, Y.-P. Lam, K.-S. Chan, Y.-Y. Yeung, Org. Lett., 2020, 22, 7353-73572.

DOI: 10.1021/acs.orglett.0c02701 (free Supporting Information)



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Abstract

Stable zwitterionic compounds catalyze a synthesis of α,α-dihalo-N-arylacetamides from β-oxo amides and N-halosuccinimides as the halogen sources. The corresponding α,α-dihalo-N-arylacetamides were obtained in very good yields under mild conditions without strong base or acid.

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Key Words

α-bromoamides, α-chloroamides, NBS, NCS, organocatalysis


ID: J54-Y2020