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Synthesis of Chiral Salen-type Ligands for Iridium Catalysts Used in C-H Bond Insertion Reactions

Hernandez Sanchez, Dalyanne N
http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1620475657966529

Abstract Details

2021, BS, Kent State University, College of Arts and Sciences / Department of Chemistry and Biochemistry.
This thesis and research study is focused on developing an alternative synthesis for the ligands in an Iridium (III)-salen complex, starting with the R-enantiomer of BINOL. The Iridium (III)-salen complex is an effective method for diastereo- and enantioselective C-H bond functionalization. Considering the high abundance of C-H bonds in nature, precise one-step substitutions of C-H bonds with C-C or C-X bonds (where X is O or N) without disruption of the surrounding molecular structure or functional group manipulation is a long-standing goal in organic synthesis, but is also a great challenge. The formylation procedure of (R)-2-hydroxy[1,1'-binaphthalene]-3-carboxaldehyde (9) proved to be especially challenging and a large number of methods were tested. Unfortunately, the Covid-19 pandemic quarantine of the Kent campus resulted in some delays with this project in Spring and Fall 2020. Consequently, all of the proposed research was not able to be completed. Nonetheless, given these unsuccessful attempts to formylate (S)-[1,1'-binaphthalen]-2-ol (6), some density functional theory (DFT) calculations were done to provide an explanation.
Christopher Fenk, Ph.D. (Advisor)
Jeffrey Mighion, Ph.D. (Committee Member)
Robin Selinger, Ph.D. (Committee Member)
Alexander Seed, Ph.D. (Committee Member)
69 p.
Chemistry

Recommended Citations

Citations

  • Hernandez Sanchez, D. N. (2021). Synthesis of Chiral Salen-type Ligands for Iridium Catalysts Used in C-H Bond Insertion Reactions [Undergraduate thesis, Kent State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1620475657966529

    APA Style (7th edition)

  • Hernandez Sanchez, Dalyanne. Synthesis of Chiral Salen-type Ligands for Iridium Catalysts Used in C-H Bond Insertion Reactions. 2021. Kent State University, Undergraduate thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1620475657966529.

    MLA Style (8th edition)

  • Hernandez Sanchez, Dalyanne. "Synthesis of Chiral Salen-type Ligands for Iridium Catalysts Used in C-H Bond Insertion Reactions." Undergraduate thesis, Kent State University, 2021. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1620475657966529

    Chicago Manual of Style (17th edition)

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This open access ETD is published by Kent State University Honors College and OhioLINK.