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Chemistry. 2016 Jul 04;22(28):9546-50. doi: 10.1002/chem.201601819. Epub 2016 Jun 07.

Hantzsch Ester as a Photosensitizer for the Visible-Light-Induced Debromination of Vicinal Dibromo Compounds.

Chemistry (Weinheim an der Bergstrasse, Germany)

Wenxin Chen, Huachen Tao, Wenhao Huang, Guoqiang Wang, Shuhua Li, Xu Cheng, Guigen Li

Affiliations

  1. Institute of Chemistry and Biomedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Xianlin Road, 163, Nanjing, China.
  2. Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Hankou Road, 22, Nanjing, China.
  3. Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Hankou Road, 22, Nanjing, China. [email protected].
  4. Institute of Chemistry and Biomedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Xianlin Road, 163, Nanjing, China. [email protected].
  5. Department of Chemistry and Biochemistry, Texas Tech University, Memorial Circle & Boston, TX 79409-1061, Lubbock, United States.

PMID: 27128783 DOI: 10.1002/chem.201601819

Abstract

The debromination of vicinal dibromo compounds to generate alkenes usually requires harsh reaction conditions and the addition of catalysts. Just recently the visible-light-induced debromination of vicinal dibromo compounds emerged as a possible alternative to commonly used methods, but the substrate scope of this reaction is limited and a photocatalyst is necessary for the successful conversion of the starting compounds. A catalyst-free visible-light-induced debromination of vicinal dibromo compounds with a base-activated Hantzsch ester as photosensitizer is reported. The method has a wide substrate scope and a broad functional-group compatibility.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Hantzsch ester; alkenes; catalyst-free reactions; debromination; visible light

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