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Green Chemistry
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DOI: 10.1039/C7GC03101G
ARTICLE
Journal Name
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Scheme 3 Proposed Reaction Mechanism.
elimination.19 Finally, reduction of the imine with in situ generated
H2S results in the formation of bisphosphinoylaminomethane
derivatives 3 with loss of sulfur element (See Figure S5). To the best
of our knowledge, the efficient imine reduction by in situ generated
H2S is unprecedented.
Conclusions
In conclusion, we have developed the first bisphosphorylation
reaction of isothiocyanates. The environmentally friendly reaction
proceeded smoothly in a solvent-free manner, and no extra
catalysts and additives are required.
A
variety of
4
bisphosphinoylaminomethanes can be readily isolated in pure by
simply washing the crude products with ethyl acetate. This protocol
is very practical and easily scaled-up, which provides a direct way
for the preparation of bisphosphoryl derivatives.
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Conflicts of interest
There are no conflicts to declare.
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Acknowledgements
This work was financially supported by the National Natural
Science Foundation of China (21372137 and 21572110), the
Key Research and Development project of Shandong province
(2017GHY15125), the Science and Technology Development
Project in University of Shandong Province (J16LC12), the
Applied Basic Research Project (Youth Special) of Qingdao (16-
5-1-98-jch), and the Research Fund of State Key Laboratory for
Marine Corrosion and Protection of Luoyang Ship Material
Research Institute (No. KF160404). Zhen-Jiang Liu and Yue-
Xiang Chen (QUST) are acknowledged for their contributions in
the synthesis of isothiocyanates.
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Notes and references
1
(a) Phosphorus Chemistry, Biochemistry and Technology, ed. D. E.
C. Corbridge, Taylor and Francis Group: London, 2012; (b)
Aminophosphonic and Aminophosphinic Acids: Chemistry and
Biological, ed. V. P. Kukhar and H. R. Hudson, Wiley and Sons:
Chichester, New York, 1−634, 2000; (c) M. Dutartre, J. Bayardon
4 | J. Name., 2012, 00, 1-3
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