Cerium-Catalyzed C–H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents
Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (...
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| Published in | Journal of the American Chemical Society Vol. 142; no. 13; pp. 6216 - 6226 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
01.04.2020
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| Subjects | |
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| Abstract | Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C–H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C–H functionalization. |
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| AbstractList | Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C-H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C-H functionalization.Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C-H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C-H functionalization. Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C–H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C–H functionalization. |
| Author | Pan, Hui Chen, Yuegang Wang, Xin Zhang, Kaining Zuo, Zhiwei An, Qing Wang, Ziyu Liu, Weimin |
| AuthorAffiliation | School of Physical Science and Technology Chinese Academy of Sciences STU & SIOM Joint Laboratory for Superintense Lasers and the Applications University of Chinese Academy of Science State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry |
| AuthorAffiliation_xml | – name: University of Chinese Academy of Science – name: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry – name: School of Physical Science and Technology – name: STU & SIOM Joint Laboratory for Superintense Lasers and the Applications – name: Chinese Academy of Sciences |
| Author_xml | – sequence: 1 givenname: Qing surname: An fullname: An, Qing organization: University of Chinese Academy of Science – sequence: 2 givenname: Ziyu surname: Wang fullname: Wang, Ziyu organization: University of Chinese Academy of Science – sequence: 3 givenname: Yuegang surname: Chen fullname: Chen, Yuegang organization: School of Physical Science and Technology – sequence: 4 givenname: Xin surname: Wang fullname: Wang, Xin organization: University of Chinese Academy of Science – sequence: 5 givenname: Kaining surname: Zhang fullname: Zhang, Kaining organization: University of Chinese Academy of Science – sequence: 6 givenname: Hui surname: Pan fullname: Pan, Hui organization: University of Chinese Academy of Science – sequence: 7 givenname: Weimin surname: Liu fullname: Liu, Weimin email: liuwm@shanghaitech.edu.cn organization: STU & SIOM Joint Laboratory for Superintense Lasers and the Applications – sequence: 8 givenname: Zhiwei orcidid: 0000-0002-3361-3220 surname: Zuo fullname: Zuo, Zhiwei email: zuozhw@shanghaitech.edu.cn organization: Chinese Academy of Sciences |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32181657$$D View this record in MEDLINE/PubMed |
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| Snippet | Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization... |
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| SubjectTerms | alcohols alkanes alkylation amination carbon-hydrogen bond activation catalysts catalytic activity cerium energy free radicals homolytic cleavage hydrogen redox reactions spectroscopy |
| Title | Cerium-Catalyzed C–H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents |
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