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Title: Palladium-catalyzed Br/D exchange of arenes: Selective deuterium incorporation with versatile functional group tolerance and high efficiency

Journal Article · · Organic Chemistry Frontiers (Online)
DOI: https://doi.org/10.1039/C5QO00181A · OSTI ID:1210145
 [1];  [1];  [1]
  1. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Science
+ Show Author Affiliations

There is a facile method for introducing one or more deuterium atoms onto an aromatic nucleus via Br/D exchange with high functional group tolerance and high incorporation efficiency is disclosed. Deuterium-labeled aryl chlorides and aryl borates which could be used as substrates in cross-coupling reactions to construct more complicated deuterium-labeled compounds can also be synthesized by this method.

Research Organization:
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)
Sponsoring Organization:
USDOE Office of Science (SC)
Grant/Contract Number:
AC05-00OR22725
OSTI ID:
1210145
Journal Information:
Organic Chemistry Frontiers (Online), Journal Name: Organic Chemistry Frontiers (Online) Journal Issue: 9 Vol. 2; ISSN 2052-4129
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 44, Issue 14 https://doi.org/10.1002/jlcr.520
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Cited By (6)

Nickel-Catalyzed Deoxygenative Deuteration of Aryl Sulfamates journal December 2016
Photokatalytische Deuterierung von Halogeniden mit D 2 O über porösen CdSe-Nanoschichten journal April 2018
Photocatalytic Deuteration of Halides Using D 2 O over CdSe Porous Nanosheets: A Mild and Controllable Route to Deuterated Molecules journal April 2018
Controllable deuteration of halogenated compounds by photocatalytic D2O splitting journal January 2018
Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes journal January 2019
Hydro/Deutero Deamination of Arylazo Sulfones under Metal- and (Photo)Catalyst-Free Conditions journal June 2019

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY