Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 28, Pages 9470-9474Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201903983
Keywords
allylic acetal; C-H functionalization; dipolar cycloaddition; indenopyrazolopyrazolone; tandem reaction
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Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIP) [2017R1A2B2004786, 2018R1D1A1B07042994, 2019R1A4A2001451]
- Institute for Basic Science [IBS-R010-A2]
- National Research Foundation of Korea [2017R1A2B2004786, 2018R1D1A1B07042994] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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The ruthenium(II)-catalyzed C-H functionalization of (hetero)aryl azomethine imines with allylic acetals is described. The initial formation of allylidene(methyl)oxoniums from allylic acetals could trigger C(sp(2))-H allylation, and subsequent endo-type [3+2] dipolar cycloaddition of polar azomethine fragments to deliver valuable indenopyrazolopyrazolones. The utility of this method is showcased by the late-stage functionalization of bioactive molecules such as estrone and celecoxib. Combined experimental and computational investigations elucidate a plausible mechanism of this new tandem reaction. Notably, the reductive transformation of synthesized compounds into biologically relevant diazocine frameworks highlights the importance of the developed methodology.
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