Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 15, Pages 2223-2229Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100212
Keywords
[3+2] annulation; C2-alkenylations; C-H functionalization; Heterocycles; Rh(III) catalyst
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The Rh(III)-catalyzed [3+2] annulations and C2-alkenylations of indoles with 1,3-diynes described in this study deliver synthetically important 3H-pyrrolo[1,2-a]indol-3-ones and highly functionalized tetrasubstituted olefin derivatives, with high efficiency and broad functional group compatibility. Additionally, the method has been successfully extended to the synthesis of bis-annulated and trisubstituted alkenes, as well as for the core structure synthesis of protein kinase C inhibitors and melatonin analogues.
Described herein is the Rh(III)- catalyzed [3+2] annulations and C2-alkenylations of indoles with 1,3-diynes, which deliver the synthetically important 3H-pyrrolo[1,2-a]indol-3-ones and highly functionalized tetrasubstituted olefin derivatives. Importantly, in this methodology, the additive controlled selective formation of desired scaffolds. This synthetic strategy exhibits high efficiency and broad functional group compatibility. Furthermore, this protocol has been successfully extended to the synthesis of bis-annulated and trisubstituted alkenes. The method is also smoothly applied for the synthesis of the core structure of protein kinase C inhibitor and melatonin analogues.
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