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Green Chemistry
Page 5 of 6
DOI: 10.1039/C6GC01318J
Journal Name
ARTICLE
acetylation, sulfonylation, and diazotization followed by
iodination and reduction. Deprotection of the amino groups
was achieved by standard alkaline hydrolysis followed by
acidification. In the case of 4-hydroxyaminobenzene, selective
methylation of the hydroxyl group could be accomplished after
We thank Professor Motomu Kanai, University of Tokyo, for
helpful discussions.
Notes and references
protecting the amino group.
1 also showed good performance
1
2
3
4
5
R. A. Sheldon, Chem. Soc. Rev., 2012, 41, 1437.
with the amino acid glycine in the protection/deprotection
processes as well as tolerance for the coupling conditions.
Compared with those obtained for traditional amine
protecting agents, the yields and reaction rates under our
conditions were significantly improved. Furthermore, 1 was
recovered in good yield after deprotection and the atom
economy of the chemical process was significantly improved.
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was successfully solved by using recoverable
1 in this study.
But the greenness of the synthesis was not entirely satisfactory
owing to the use of organic solvents, inorganic base and acid
to recover 1. Thus, the greenness of the entire process needs
to be further improved. However, the approach of a “direct
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a chemical process,
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1 was used
,
for the atom-economical Gabriel-type synthesis of various
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consumed, and
1
was recovered in nearly quantitative yield.
for the synthesis of O-alkylated
Further application of
1
hydroxylamines reactions featured a broad substrate scope
and generally afforded the products in good to excellent yields.
As part of our new approach, 1 showed good performance as a
recoverable protecting agent for aliphatic and aromatic
primary amines. The high protection/deprotection and
recovery yields of
conventional amine protecting reagents. Efforts including the
application of to the construction of other potentially
valuable organic molecules and the immobilization of on
1 make it a valuable complement to
1
1
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Acknowledgements
We gratefully acknowledge the National S&T Major Project
(2012ZX09103101-060), the National Natural Science
Foundation of China (81502932), and the Shenyang Science &
Technology Bureau Item (No. F13-316-1-56) for generous
financial support. This work was also supported by Program for
Innovative Research Team of the Ministry of Education and
Program for Liaoning Innovative Research Team in University.
This journal is © The Royal Society of Chemistry 20xx
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