Journal
GREEN CHEMISTRY
Volume 22, Issue 20, Pages 7023-7030Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0gc02347g
Keywords
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Funding
- National Natural Science Foundation of China [21772109, 21971140]
- Major National Science and Technology Program of China for Innovative Drug [2018ZX09711001-005-007, 2017ZX09101002-001-001]
- Foshan-Tsinghua Innovation Special Fund (FTISF)
- Tsinghua Xuetang Talents Program
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An unprecedented photoinduced azide-alkene cycloaddition has been developed, the key elements of which include the photoisomerization of cis-cycloheptenone to trans-cycloheptenone, strain-promoted 1,3-dipolar cycloaddition of trans-cycloheptenone with azide, and aerobic oxidative aromatization of the resulting 1,2,3-triazoline. The newly developed photoclick reactions display several appealing features including high overall efficiency, broad substrate scope, environmentally benign conditions, and operational simplicity, which provide an enabling tool for accessing structurally diverse 1,2,3-triazoles. In addition, the photoisomerization-cycloaddition strategy could also be extended to the 1,3-dipolar cycloadditions of trans-cyclooctenone with azide andtrans-cycloheptenone with nitrile oxide. More appealingly, the title reaction has been successfully applied as a bioconjugation tool for in vitro protein labeling.
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