Programmable Deuteration of Indoles via Reverse Deuterium Exchange

Methods for selective deuterium incorporation into drug-like molecules have become extremely valuable due to the commercial, mechanistic, and biological importance of deuterated compounds. Herein, we report a programmable labeling platform that allows access to C2, C3, or C2- and C3-deuterated indol...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 15; pp. 10772 - 10776
Main Authors Fitzgerald, Liam S., McNulty, Rachael L., Greener, Andrew, O’Duill, Miriam L.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.08.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
SUBSTITUTION
ACTIVATION
HETEROCYCLES
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Summary:Methods for selective deuterium incorporation into drug-like molecules have become extremely valuable due to the commercial, mechanistic, and biological importance of deuterated compounds. Herein, we report a programmable labeling platform that allows access to C2, C3, or C2- and C3-deuterated indoles under mild, user-friendly conditions. The C2-deuterated indoles are accessed using a reverse hydrogen isotope exchange strategy which represents the first non-directed C2-deuteration of indoles.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00819