Abstract
Ag2CO3-catalyzed hydrogen isotope exchange of five-membered heteroarenes is disclosed. The reaction can be conducted in the open air, at ambient temperature, and with D2O as deuterium source. Moreover, this protocol showed orthogonal site selectivity to existing technology, thereby greatly expanding the scope of substrates for HIE reaction. The mechanistic study indicated that the carbonate group plays a crucial role to achieve high levels of deuterium incorporation by lowering the activation energy of H/D exchange process.
| Original language | English |
|---|---|
| Pages (from-to) | 6745-6749 |
| Number of pages | 5 |
| Journal | Organic Letters |
| Volume | 21 |
| Issue number | 17 |
| DOIs | |
| State | Published - Sep 6 2019 |
| Externally published | Yes |
Funding
We thank the National Natural Science Foundation of China (Grant No. 21704041), Major Program of Natural Science Research of Jiangsu Higher Education Institutions of China (No.18KJA150005), and Natural Science Foundation of Jiangsu Province (No.BK20181373) for support. We thank Peter V. Bonnesen and Kunlun Hong (Oak Ridge National Laboratory) for assistance with the preparation of the manuscript. We thank the National Natural Science Foundation of China (Grant No. 21704041), Major Program of Natural Science Research of Jiangsu Higher Education Institutions of China (No.18KJA150005) and Natural Science Foundation of Jiangsu Province (No.BK20181373) for support. We thank Peter V. Bonnesen and Kunlun Hong (Oak Ridge National Laboratory) for assistance with the preparation of the manuscript.