Citation: Hua Tian, Xin Yang, Ge Shi, Heng Xu, Yi Dong. Rhodium-catalyzed site-selective cross-couplings of indoles and pyridotriazoles through carbene insertion[J]. Chinese Chemical Letters, ;2025, 36(7): 110434. doi: 10.1016/j.cclet.2024.110434 shu

Rhodium-catalyzed site-selective cross-couplings of indoles and pyridotriazoles through carbene insertion

Hua Tian ^{a, b, c, 1} ,
Xin Yang ^{a, b, c, 1} ,
Ge Shi ^{a, b, c} ,
Heng Xu ^{a, b, c, *,} ,
Yi Dong ^{a, b, c, *,}

a.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
c.
Key Laboratory of Small Molecule Immuno-Oncology Drug Discovery, Chinese Academy of Medical Sciences, Beijing 100050, China

xuheng@imm.ac.cn

dongyi@imm.ac.cn

Received Date: 30 April 2024
Revised Date: 2 September 2024
Accepted Date: 8 September 2024
Available Online: 11 September 2024

Figures(6)

The switchable cross-coupling of indoles and pyridotriazoles through carbene insertion at C₂- or C₃-positon has been developed in this paper. This highly site-selective C−H carbenoid functionalization is determined by both the Rh-catalyst species and auxiliary groups. [Cp^*RhCl₂]₂ and coordinating pyrimidyl group direct the C−H carbenoid functionalization to occur at the C₂-position, while Rh₂OAc₄ and non-coordinating benzyl group lead the reaction to occur at the C₃-position of the indoles. This regioselective C−H functionalization strategy is of significant importance for the discovery of indole drugs.
- Rhodium-catalyzed,
- Site-selective,
- Cross-couplings,
- Carbene insertion,
- Pyridotriazoles
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