Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes

Guo, Lei; Xu, Chen; Wu, Ding-Chuan; Hu, Guang-Qi; Zhang, Hong-Hai; Hong, Kunlun; Chen, Su; Liu, Xiang

doi:10.1039/C9CC03988K

Title: Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes

Journal Article · 25 June 2019 · ChemComm

DOI: https://doi.org/10.1039/C9CC03988K · OSTI ID:1546519

Guo, Lei ^[1]; Xu, Chen ^[1]; Wu, Ding-Chuan ^[1]; Hu, Guang-Qi ^[1];

^[1]; Hong, Kunlun ^[2];

^[1]; Liu, Xiang ^[1]

Nanjing Tech. Univ. Nanjing (China)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

An efficient approach for synthesizing congested deuterium-labeled arenes via cascade alkylation and deuteration with aryl iodides has been disclosed. Here, we found that the adoption of sodium formate-$$d$$ as a deuterium source is the key for achieving high deuterium incorporation >98%.

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

Sponsoring Organization:: USDOE Office of Science (SC); National Natural Science Foundation of China (NNSFC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1546519

Journal Information:: ChemComm, Journal Name: ChemComm Journal Issue: 59 Vol. 55; ISSN CHCOFS; ISSN 1359-7345

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Visible-light-mediated hydrodehalogenation and Br/D exchange of inactivated aryl and alkyl halides with a palladium complex Zhou, Zhao-Zhao; Zhao, Jia-Hui; Gou, Xue-Ya Organic Chemistry Frontiers, Vol. 6, Issue 10 https://doi.org/10.1039/C9QO00240E	journal	January 2019
Symmetrical and unsymmetrical 2,6-dialkyl-1,1′-biaryls by combined catalysis of aromatic alkylation via palladacycles and Suzuki-type coupling Catellani, Marta; Motti, Elena; Minari, Monica Chemical Communications, Issue 2 https://doi.org/10.1039/a909099a	journal	January 2000
Selective deuteration of (hetero)aromatic compounds via deutero-decarboxylation of carboxylic acids Grainger, Rachel; Nikmal, Arif; Cornella, Josep Organic & Biomolecular Chemistry, Vol. 10, Issue 16 https://doi.org/10.1039/c2ob25157d	journal	January 2012
Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds Loh, Yong Yao; Nagao, Kazunori; Hoover, Andrew J. Science, Vol. 358, Issue 6367 https://doi.org/10.1126/science.aap9674	journal	November 2017

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