Cu(II)-Catalyzed H/D exchange of indole derivatives

Jing Wen Bai, Lei Guo, Meng Zhe Chen, Rigoberto Advincula, Hong Hai Zhang

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Cu(OTf)2 was explored as an efficient catalyst for hydrogen deuterium (H/D) exchange of indole derivatives. The advantage of this reaction is that deuteration selectivity can be adjusted by changing reaction parameters. When the reaction was performed with 10 mol% of Cu(OTf)2 as a catalyst in dioxane at 80 °C, deuteration preferentially occurred at C3 position of indole with high atom% deuterium incorporation. Furthermore, per-deuterated indole derivatives could be achieved by performing the reaction with higher catalyst loading in toluene at 120 °C. Performing the reaction on a continuous flow reactor facilitates the scale-up process, affording deuterated products with a throughput of 3.9 g/h.

Original languageEnglish
Article number154884
JournalTetrahedron Letters
Volume135
DOIs
StatePublished - Jan 31 2024

Funding

Continuous flow research was supported by Center for Nanophase Materials Sciences (CNMS), which is a US Department of Energy , Office of Science User Facility at Oak Ridge National Laboratory . This research was started when Hong-Hai Zhang was a professor at Nanjing Tech University . Dr. Hong-Hai Zhang completed the manuscript while a research staff scientist at Oak Ridge National Laboratory . Dr. Hong-Hai Zhang is supported by the Center for Structural Molecular Biology, sponsored by the Office of Biological and Environmental Research . We thank the National Natural Science Foundation of China (Grant Numbers 22075135 ). Continuous flow research was supported by Center for Nanophase Materials Sciences (CNMS), which is a US Department of Energy, Office of Science User Facility at Oak Ridge National Laboratory. This research was started when Hong-Hai Zhang was a professor at Nanjing Tech University. Dr. Hong-Hai Zhang completed the manuscript while a research staff scientist at Oak Ridge National Laboratory. Dr. Hong-Hai Zhang is supported by the Center for Structural Molecular Biology, sponsored by the Office of Biological and Environmental Research. We thank the National Natural Science Foundation of China (Grant Numbers 22075135).

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