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

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

doi:10.1021/acs.orglett.3c00883

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

Journal Article · Wed Apr 26 00:00:00 EDT 2023 · Organic Letters

DOI:https://doi.org/10.1021/acs.orglett.3c00883· OSTI ID:1976038

Gu, Jian-Guo ^[1]; Wang, Cai-Xia ^[1]; Hu, Guang-Qi ^[1]; Shen, Kang ^[1]; ^[2]

Nanjing Tech Univ. (China)
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)

Here, 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.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER); National Natural Science Foundation of China (NSFC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1976038

Journal Information:: Organic Letters, Journal Name: Organic Letters Journal Issue: 17 Vol. 25; ISSN 1523-7060

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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