4.8 Review

Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions

Journal

CHEMICAL REVIEWS
Volume 121, Issue 1, Pages 110-139

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrev.0c00160

Keywords

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Funding

  1. National Natural Science Foundation of China [21901142]
  2. Natural Science Foundation of Shandong Province [ZR2019QB001]
  3. Key Research and Development Program of Shandong Province [2017CXGC1401]
  4. Natural Science Foundation of Jiangsu Province [BK20180227]
  5. Fundamental Research Funds of Shandong University [21310088963023, 2020QNQT007, 2020QNQT009]
  6. NSF Graduate Research Fellowship Program
  7. NIH [R01 GM088285]

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This review focuses on transition metal-catalyzed methodologies and applications involving the cleavage of C-C bonds in vinylcyclopropanes (VCPs) for cycloaddition and related addition reactions. It discusses the properties of activated and nonactivated VCPs, transition metal-catalyzed cycloadditions, and addition reactions, as well as challenges and potential opportunities in the field.
In this review, transition metal-catalyzed methodologies and applications that exploit C-C bond cleavage of vinylcyclopropanes (VCPs) are summarized with a focus on cycloaddition and related addition reactions. Transition metals, including palladium, nickel, iron, ruthenium, rhodium, cobalt, and iridium, can catalyze the cleavage of C-C bonds in activated or nonactivated VCPs. Additionally, these bond-breaking reactions can occur as intraor intermolecular processes. The properties of activated and nonactivated VCPs are discussed in the Introduction. Various transition metal-catalyzed cycloaddition and addition reactions involving the cleavage of C-C bonds in activated VCPs are then discussed in the next chapter. The transition metal-catalyzed cycloadditions involving the cleavage of C-C in nonactivated VCPs are summarized in the following chapter. Finally, challenges and potential opportunities are outlined in the last chapter.

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