Pd-Catalyzed Regioselective Deuteration of Indole’s C4-Position with Transient Directing Groups

As a representative scaffold of alkaloids, indoles have been extensively subjected to deuteration, but the regioselective C4 labeling has not been achieved due to its low reactivity. In this work, a Pd-catalyzed deuterium labeling at the indole’s C4 position has been developed under the strategy of...

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Published inJournal of organic chemistry Vol. 88; no. 24; pp. 17164 - 17171
Main Authors Zheng, Chenxu, Jiang, Zhi-Jiang, Jin, Ke, Wang, Qian, Bai, Jian-Fei, Xu, Gang, Gao, Zhanghua
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.12.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DRUG
ACTIVATION
FUNCTIONALIZATIONS
HETEROCYCLES
EXCHANGE
DEUTERIUM
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Summary:As a representative scaffold of alkaloids, indoles have been extensively subjected to deuteration, but the regioselective C4 labeling has not been achieved due to its low reactivity. In this work, a Pd-catalyzed deuterium labeling at the indole’s C4 position has been developed under the strategy of transient directing, using D2O as a deuterium source. The substituent effect is found to be crucial in facilitating this H/D exchange process, where the reversing C–D bond formation favors an electron-enriched ligation contrary to its C–H halogenation counterpart.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02030