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    Literature Presentation 24-04-20

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    Antonis Messinis
    The document summarizes research on the use of chromium in catalytic C-H activation and cross-coupling reactions. It discusses how chromium has been used to catalyze reactions such as alkynylation, allylation, and naphthalenation through a proposed mechanism involving formation of a bis-cyclometalated chromium complex. Reaction optimization and scope are described for the alkynylation, allylation, and naphthalenation reactions. Kinetics experiments and conclusions about the reaction mechanism are also summarized. Overall, the document outlines the development of a chromium-based strategy for homocoupling-free twofold C-H activation and cross-couplings that provides selectively to synthetically useful products.

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    Literature Presentation 24-04-20

    Uploaded by

    Antonis Messinis
    9 views15 pages
    The document summarizes research on the use of chromium in catalytic C-H activation and cross-coupling reactions. It discusses how chromium has been used to catalyze reactions such as alkynylation, allylation, and naphthalenation through a proposed mechanism involving formation of a bis-cyclometalated chromium complex. Reaction optimization and scope are described for the alkynylation, allylation, and naphthalenation reactions. Kinetics experiments and conclusions about the reaction mechanism are also summarized. Overall, the document outlines the development of a chromium-based strategy for homocoupling-free twofold C-H activation and cross-couplings that provides selectively to synthetically useful products.

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    Literature presentation 24-04-20

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    The document summarizes research on the use of chromium in catalytic C-H activation and cross-coupling reactions. It discusses how chromium has been used to catalyze reactions such as alkynylation, allylation, and naphthalenation through a proposed mechanism involving formation of a bis-cyclometalated chromium complex. Reaction optimization and scope are described for the alkynylation, allylation, and naphthalenation reactions. Kinetics experiments and conclusions about the reaction mechanism are also summarized. Overall, the document outlines the development of a chromium-based strategy for homocoupling-free twofold C-H activation and cross-couplings that provides selectively to synthetically useful products.

    Copyright:

    © All Rights Reserved
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    9 views15 pages

    Literature Presentation 24-04-20

    Uploaded by

    Antonis Messinis
    The document summarizes research on the use of chromium in catalytic C-H activation and cross-coupling reactions. It discusses how chromium has been used to catalyze reactions such as alkynylation, allylation, and naphthalenation through a proposed mechanism involving formation of a bis-cyclometalated chromium complex. Reaction optimization and scope are described for the alkynylation, allylation, and naphthalenation reactions. Kinetics experiments and conclusions about the reaction mechanism are also summarized. Overall, the document outlines the development of a chromium-based strategy for homocoupling-free twofold C-H activation and cross-couplings that provides selectively to synthetically useful products.

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    of 15

    Literature Presentation III

    Antonis Messinis

    24-04-20

    1
    1. Introduction to Chromium

    • The 7th most abundant transition metal • Biologically active (glucose metabolism)
    • Inexpensive: 3 times cheaper than Co • Widely used: metallurgy, pigments, catalysis
    • Cr(III) is non toxic (but Cr(VI) is!) • The hardest metal on earth

    S
    • Nozaki−Hiyama−Kishi coupling between allyl cross couplings (Knochel et al.)
    halides and aldehydes • Olefin polymerization and selective
    • Takai olefination for conversion of aldehydes oligomerization: Chevron-Phillips ethylene
    to alkenes (not catalytic) trimerization system (250 kt 1-hexene/year)
    P • Cr mediated C(sp2) - C(sp2) Kumada type

    2
    2. Chromium: a rare metal in catalytic C-H activation

    • First examples by Knochel et al., Org. Lett., 2014:

    • Yoshikai et al., 2016-2017:

    3
    Kuzmina, O. M.; Knochel. Org. Lett. 2014, 16, 5208; Yan, J.; Yoshikai. Org. Lett. 2017, 19, 6630; Yan, J.; Yoshikai. Org. Chem. Front. 2017, 4, 1972;
    2. Chromium: a rare metal in catalytic C-H activation

    • Zheng et al., 2017: • Yamazaki et al., 1999:

    • Fuchs et al., 2002:

    4
    Li, Y.; Deng, G.; Zeng, X., Organometallics 2016, 35, 747; Yamazaki, S., Org. Lett. 1999, 1, 2129; Lee, S.; Fuchs, P. L., J. Am. Chem. Soc. 2002, 124, 13978.
    3.

    5
    4. Reaction optimization

    PMB =
    O

    TES = -SiEt3
    6
    5. Alkynylation reaction and scope

    7
    6. Allylation reaction and scope

    8
    7. Naphthalenation reaction and scope

    9
    7. Mechanism: formation of a putative bis-cyclometalated Cr
    complex

    10
    7. Mechanism: formation of a putative bis-cyclometalated Cr
    complex

    11
    8. Mechanism: kinetics of the reaction

    12
    9. Mechanism: conclusions and proposed cycle

    13
    10. Summary

    • Fe-based strategy for homocoupling-free twofold C–H


    activation/crosscouplings
    • Excellent cross-coupling selectivity with stoichiometric reagents
    • Products relevant to materials science
    • Suggested mechanism supported by H/D experiments

    14
    Thank you for your attention !

    15

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