Hypervalent Iodine Reagent for Introduction of Indoles via C-H activation of Arenes

N-H-indole BX is a stable hypervalent iodine compound used for the introduction of an indole ring via C-H bond activation of (hetero)arenes.¹⁾ In the presence of a rhodium or ruthenium catalyst, N-H-indole BX can be used to regioselectively introduce an indole ring into arenes with directing groups. In this reaction, the indole ring can be introduced in a manner that is difficult to achieve with conventional methods due to the indole ring’s natural nucleophilicity. Furthermore, the indole ring is introduced at the 6-position and 8-position of pyridinones and quinoline-N-oxides, respectively.²⁾ Thus, N-H-indole BX is expected to be used for drug discovery research.

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References

• 1) Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung
  • P. Caramenti, S. Nicolai, J. Waser, Eur. J. Org. Chem. 2017, 23, 14702.
• 2) Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents
  • E. Grenet, A. Das, P. Caramenti, J. Waser, Beilstein J. Org. Chem. 2018, 14, 1208.

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