Abstract
A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(I)/Pd(0)/Cu(II) catalysis. 2-Iodoanilines and phenols undergo a Cu(I)/Pd(0)-catalyzed Sonogashira reaction with ethynyl BMIDA followed by in situ Cu(II)-catalyzed 5-endo-dig cyclization to generate heterocyclic scaffolds with a BMIDA functional group in the 2-position. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.
| Original language | English |
|---|---|
| Pages (from-to) | 8703-8706 |
| Number of pages | 4 |
| Journal | Chemical Communications |
| Issue number | 56 |
| Early online date | 16 Jun 2016 |
| DOIs | |
| Publication status | Published - 18 Jul 2016 |
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Keywords
- one-pot cascade reaction
- Sonogashira
- heterocyclic scaffolds
- borylated indoles
- benzofurans
- aza-derivatives
- BMIDA functional group
Cite this
Seath, C. P., Wilson, K. L., Campbell, A., Mowat, J. M., & Watson, A. J. B. (2016). Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(I)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols. Chemical Communications, (56), 8703-8706. https://doi.org/10.1039/C6CC04554E