K2CO3/18-Crown-6-Catalyzed Selective H/D Exchange of Heteroarenes with Bromide as a Removable Directing Group

Jian Guo Gu, Cai Xia Wang, Guang Qi Hu, Kang Shen, Hong Hai Zhang

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7 Scopus citations

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 languageEnglish
Pages (from-to)3055-3059
Number of pages5
JournalOrganic Letters
Volume25
Issue number17
DOIs
StatePublished - 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).

FundersFunder 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 China22075135
Nanjing Tech University

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