Journal
JOURNAL OF MATERIALS CHEMISTRY A
Volume 10, Issue 15, Pages 8268-8272Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ta01146h
Keywords
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Funding
- National Natural Science Foundation of China [22175093]
- Large Equipment Open Funding of Nanjing University of Science and Technology
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A facile and efficient nitrogen-centered-radical-mediated approach to cleave C-N bonds in a monocyclic pyrazole has been described. The reaction achieved high yields and led to an energetic compound with promising application prospects.
C-N bond activation has been recognized as a powerful methodology in organic synthesis, but C-N bond activation on monocyclic rings remains an intractable challenge, due to the high energy barrier required for the dearomatization process. Now a facile and efficient nitrogen-centered-radical-mediated approach to cleave C-N bonds in a monocyclic pyrazole is described. Using N-bromosuccinimide as a radical initiator, C-N bond cleavage was achieved in yields up to 91%. This reaction Led to an important precursor (2), subsequently annulated and oxidized to an energetic compound 4, which exhibits promising application in balancing performances and thermal stabilities.
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