Display options
Cite
Liu WB, Chen C, Zhang Q, et al. Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides. Beilstein J Org Chem. 2012;8:344-8doi: 10.3762/bjoc.8.38.
Liu, W. B., Chen, C., Zhang, Q., & Zhu, Z. B. (2012). Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides. Beilstein journal of organic chemistry, 8344-8. https://doi.org/10.3762/bjoc.8.38
Liu, Wei-Bing, et al. "Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides." Beilstein journal of organic chemistry vol. 8 (2012): 344-8. doi: https://doi.org/10.3762/bjoc.8.38
Liu WB, Chen C, Zhang Q, Zhu ZB. Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides. Beilstein J Org Chem. 2012;8:344-8. doi: 10.3762/bjoc.8.38. Epub 2012 Mar 07. PMID: 22509203; PMCID: PMC3326611.
Copy Download .nbib Format: NLM
Share it on

Beilstein J Org Chem. 2012;8:344-8. doi: 10.3762/bjoc.8.38. Epub 2012 Mar 07.

Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides.

Beilstein journal of organic chemistry

Wei-Bing Liu, Cui Chen, Qing Zhang, Zhi-Bo Zhu

Affiliations

  1. School of Chemistry and Life Science, Guangdong University of Petrochemical Technology, Maoming 525000, China.

PMID: 22509203 PMCID: PMC3326611 DOI: 10.3762/bjoc.8.38

Abstract

A novel and reliable method for the direct preparation of 2,2-dihalo-N-phenylacetamides is reported. The key transformation involves the cleavage of a carbon-carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this method significantly expands the value of DIB as a unique and powerful tool in chemical synthesis. This protocol not only adds a new aspect to reactions that use other hypervalent iodine reagents but also provides a wide space for the synthesis of disubstituted acetamides.

Keywords: (diacetoxyiodo)benzene; 3-oxo-N-phenylbutanamides; cleavage of carbon–carbon bond; difunctionalized acetamides; novel oxidation

References

  1. Angew Chem Int Ed Engl. 2006 Jul 3;45(27):4402-4 - PubMed
  2. Chem Rev. 2002 Jul;102(7):2523-84 - PubMed
  3. J Org Chem. 2005 Apr 15;70(8):2893-903 - PubMed
  4. Angew Chem Int Ed Engl. 2009;48(48):9052-70 - PubMed
  5. Org Lett. 2010 Apr 2;12(7):1492-5 - PubMed
  6. Chem Commun (Camb). 2009 Apr 28;(16):2086-99 - PubMed
  7. Chem Commun (Camb). 2011 Jan 7;47(1):102-15 - PubMed
  8. Angew Chem Int Ed Engl. 2011 Feb 1;50(5):1059-63 - PubMed
  9. Org Lett. 2011 Jul 1;13(13):3406-9 - PubMed
  10. Beilstein J Org Chem. 2011;7:1436-40 - PubMed
  11. Angew Chem Int Ed Engl. 2010 Mar 15;49(12):2175-7 - PubMed
  12. Chem Commun (Camb). 2009 Apr 28;(16):2073-85 - PubMed
  13. Chem Rev. 2008 Dec;108(12):5299-358 - PubMed
  14. Chem Rev. 1996 May 9;96(3):1123-1178 - PubMed
  15. Angew Chem Int Ed Engl. 2005 Jun 13;44(24):3656-65 - PubMed
  16. Angew Chem Int Ed Engl. 2009;48(24):4332-6 - PubMed
  17. J Am Chem Soc. 2011 Oct 19;133(41):16410-3 - PubMed
  18. Org Lett. 2011 Dec 16;13(24):6504-7 - PubMed

Publication Types