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

Abstract

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%.

Authors:
 [1];  [1];  [1];  [1]; ORCiD logo [1];  [2]; ORCiD logo [1];  [1]
  1. Nanjing Tech. Univ. Nanjing (China)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC); National Natural Science Foundation of China (NNSFC)
OSTI Identifier:
1546519
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
ChemComm
Additional Journal Information:
Journal Volume: 55; Journal Issue: 59; Journal ID: ISSN 1359-7345
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Guo, Lei, Xu, Chen, Wu, Ding-Chuan, Hu, Guang-Qi, Zhang, Hong-Hai, Hong, Kunlun, Chen, Su, and Liu, Xiang. Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes. United States: N. p., 2019. Web. doi:10.1039/C9CC03988K.
Guo, Lei, Xu, Chen, Wu, Ding-Chuan, Hu, Guang-Qi, Zhang, Hong-Hai, Hong, Kunlun, Chen, Su, & Liu, Xiang. Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes. United States. doi:10.1039/C9CC03988K.
Guo, Lei, Xu, Chen, Wu, Ding-Chuan, Hu, Guang-Qi, Zhang, Hong-Hai, Hong, Kunlun, Chen, Su, and Liu, Xiang. Tue . "Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes". United States. doi:10.1039/C9CC03988K.
@article{osti_1546519,
title = {Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes},
author = {Guo, Lei and Xu, Chen and Wu, Ding-Chuan and Hu, Guang-Qi and Zhang, Hong-Hai and Hong, Kunlun and Chen, Su and Liu, Xiang},
abstractNote = {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%.},
doi = {10.1039/C9CC03988K},
journal = {ChemComm},
number = 59,
volume = 55,
place = {United States},
year = {2019},
month = {6}
}

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    Works referencing / citing this record:

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    journal, November 2015


    Nickel-Catalyzed Deoxygenative Deuteration of Aryl Sulfamates
    journal, December 2016

    • Kuriyama, Masami; Kujirada, Shota; Tsukuda, Kotaro
    • Advanced Synthesis & Catalysis, Vol. 359, Issue 6
    • DOI: 10.1002/adsc.201601105

    The Renaissance of H/D Exchange
    journal, October 2007

    • Atzrodt, Jens; Derdau, Volker; Fey, Thorsten
    • Angewandte Chemie International Edition, Vol. 46, Issue 41
    • DOI: 10.1002/anie.200700039

    Cryptocatalytic 1,2-Alkene Migration in a σ-Alkyl Palladium Diene Complex
    journal, July 2009

    • Evans, Louise A.; Fey, Natalie; Lloyd-Jones, Guy C.
    • Angewandte Chemie International Edition, Vol. 48, Issue 34
    • DOI: 10.1002/anie.200901468

    On the Interpretation of Deuterium Kinetic Isotope Effects in CH Bond Functionalizations by Transition-Metal Complexes
    journal, March 2012

    • Simmons, Eric M.; Hartwig, John F.
    • Angewandte Chemie International Edition, Vol. 51, Issue 13
    • DOI: 10.1002/anie.201107334

    Palladium-Catalyzed ortho -Selective CH Deuteration of Arenes: Evidence for Superior Reactivity of Weakly Coordinated Palladacycles
    journal, November 2013

    • Ma, Sandy; Villa, Giorgio; Thuy-Boun, Peter S.
    • Angewandte Chemie International Edition, Vol. 53, Issue 3
    • DOI: 10.1002/anie.201305388

    Ortho CH Acylation of Aryl Iodides by Palladium/Norbornene Catalysis
    journal, September 2015

    • Dong, Zhe; Wang, Jianchun; Ren, Zhi
    • Angewandte Chemie International Edition, Vol. 54, Issue 43
    • DOI: 10.1002/anie.201506397

    Palladium-Catalyzed Catellani ortho -Acylation Reaction: An Efficient and Regiospecific Synthesis of Diaryl Ketones
    journal, September 2015

    • Huang, Yunze; Zhu, Rui; Zhao, Kun
    • Angewandte Chemie International Edition, Vol. 54, Issue 43
    • DOI: 10.1002/anie.201506446

    Palladium-Catalyzed Heteroarylation and Concomitant ortho -Alkylation of Aryl Iodides
    journal, September 2015

    • Lei, Chuanhu; Jin, Xiaojia; Zhou, Jianrong Steve
    • Angewandte Chemie International Edition, Vol. 54, Issue 45
    • DOI: 10.1002/anie.201507128

    Iridium-Catalyzed Formyl-Selective Deuteration of Aldehydes
    journal, June 2017

    • Kerr, William J.; Reid, Marc; Tuttle, Tell
    • Angewandte Chemie International Edition, Vol. 56, Issue 27
    • DOI: 10.1002/anie.201702997

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    C−H Functionalisation for Hydrogen Isotope Exchange
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    Epoxides as Alkylating Reagents for the Catellani Reaction
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