Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 20, Pages 4756-4760Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201605335
Keywords
alkynes; cylopropenation; diazo surrogates; N-nosylhydrazones; silver
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Funding
- NSFC [21522202, 21502017, 21372038]
- Ministry of Education of the People's Republic of China [NCET-13-0714]
- Jilin Provincial Research Foundation for the Basic Research [20140519008JH]
- Fundamental Research Funds for Central Universities [2412015BJ005, 2412015KJ013, 2412016KJ040]
- Jilin Province Key Laboratory of Organic Functional Molecular Design Synthesis [130028658]
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The [2+1] cycloaddition of alkynes with diazo compounds represents one of the most powerful and reliable methods for the construction of cyclopropenes. However, it remains a formidable challenge to accomplish the cyclopropenation of alkynes with non-stabilized diazoalkanes, owing to the fact that such compounds are unstable and prone to detonation. Herein, we report a general silver-catalyzed cyclopropenation reaction of alkynes with unstable diazoalkanes, by for the first time the discovery and application of N-nosylhydrazones as room-temperature decomposiable diazo surrogates. This method allows for the efficient assembly a wide variety of cyclopropene derivatives that are otherwise difficult to access by conventional methods.
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