Abstract
The K2CO3/18-crown-6-catalyzed H/D exchange of heretoarenes in high atom % deuterium incorporation is disclosed. The use of a weak base as a catalyst leads to excellent site selectivity and broad functional group tolerance. Control experiments indicated that the use of bromide, which enhances the adjacent C-H bond reactivity, as a removable directing group is essential. Moreover, conversion of bromide to other functional groups is also performed to construct other useful deuterated compounds.
| Original language | English |
|---|---|
| Pages (from-to) | 3055-3059 |
| Number of pages | 5 |
| Journal | Organic Letters |
| Volume | 25 |
| Issue number | 17 |
| DOIs | |
| State | Published - May 5 2023 |
Funding
This research was started when H.-H.Z. was a professor at Nanjing Tech University, and H.-H.Z. completed the manuscript while a research staff scientist at Oak Ridge National Laboratory. H.-H.Z. is currently supported by the Center for Structural Molecular Biology, sponsored by the Office of Biological and Environmental Research and supported by the Center for Nanophase Materials Sciences, which is a DOE Office of Science User Facility. We thank the National Natural Science Foundation of China (Grant 22075135).
| Funders | Funder number |
|---|---|
| Center for Nanophase Materials Sciences | |
| Center for Structural Molecular Biology | |
| Office of Science | |
| Biological and Environmental Research | |
| Oak Ridge National Laboratory | |
| National Natural Science Foundation of China | 22075135 |
| Nanjing Tech University |