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Volume 3, Issue 2 (Suppl) Trends in Green chem
ISSN: 2471-9889 Environmental & Green Chemistry 2017
July 24-26, 2017
Page 104
5 th International Conference on
6 th International Conference on
July 24-26, 2017 Rome, Italy
Environmental Chemistry and Engineering
Green Chemistry and Technology
&
Metal-free aerobic oxidative coupling of thiols for synthesis of disulfides and sulfenamides
Liting Yang, Yingchao Dou, Xin Huang, Shan Zhen, Lijuan Song, Heng Li, Panke Zhang, Bingxin Yuan and Guanyu Yang
Zhengzhou University, China
Statement of the Problem: Catalytic synthesis of organic sulfenamides and disulfides has great significance and value in
synthetic chemistry and bioscience. Despite the prominent applications of sulfenamides, there are only a few reports
about their preparation. In this contribution, we reported an oxidative coupling of 2-mercaptobenzothiazole leading to
2,2-disbenzothiazoledisulfide in up to 94 % yield.
Findings: The reactions used TEMPO as the catalyst and underwent a radical mediated process. Inspired by that finding,
we explored the radical reaction between thiols and amines. Fortunately, we found a TEMPO-catalyzed aerobic oxidative
coupling system, which utilizes environmentally friendly and naturally abundant O2, producing sulfonamides and
disulfides in high yields. Reactions showed good tolerance toward various amines and thiols. Activation of the N-H bond by
2,2-disbenzothiazoledisulfide showed the great potential in organic synthesis.
Conclusion & Significance: We successfully developed a highly efficient and sustainable metal-free radical-medicated method
to generate compounds containing S-N and S-S bonds in high yields. The TEMPO-catalyzed aerobic oxidative homocoupling of
thiols or heterocoupling of thiols with amines provides a new prospect for large-scale syntheses of disulfides and sulfenamines,
such as rubber accelerator TBBS, which is required in metric tons worldwide each year.
Biography
Liting Yang is pursuing her PHD at College of Chemistry and Molecular Engineering, Zhengzhou University, China. She obtained Bachelor’s degree of Chemistry
at 2011 from Zhengzhou University. Starting from 2011 to present, she has been working on scientific research in the group of Professor Guanyu Yang. The
mian research fields contain the synthesis and application of radical catalysis and aerobic oxidative green-catalyzed construction of S-N/S-S bonds. Some of the
research achievements have been published on the international journals, such as Green Chemistry, Asian Journal of Organic Chemistry and so on.
Biography
Guanyu Yang is a Professor in College of Chemistry and Molecular Engineering, Zhengzhou University, China, since 2006. He received his Ph.D. of chemistry
in 2005 from Dalian Institute of Physical Chemistry, Chinese Academy of Sciences. His research interests center around the development of new synthetic
methodologies, and the more environmentally benign processes for the synthesis of higher added-value chemicals. For this aim, his research directs towards the
fundamental and applicable investigations of various catalytic techniques, involving organo-, biomimetic, heterogenous, and homogenous catalysis, as well as
the interdisciplinary approach. Much of his work is devoted to the development of novel synthetic methods via the catalytic oxidation with molecular oxygen as a
terminal oxidant.
Liting Yang et al., Trends in Green chem, 3:2
DOI: 10.21767/2471-9889-C1-003