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Difluoroboronate Urea-Induced Acid Amplification for Insertion Chemistry

Couch, Erica Dawn
http://rave.ohiolink.edu/etdc/view?acc_num=osu1404225572

Abstract Details

2014, Master of Science, Ohio State University, Chemistry.
Development of a new enhanced boronate urea that benefits from internal coordination of the urea carbonyl to a strategically placed Lewis acid has enabled a new direction in hydrogen bond donor (HBD) catalysis. Activation of a-nitrodiazocarbonyl compounds has elicited carbene-like reactivity, allowing for access to metal-free insertion reactions. Recent developments have utilized the difluroboronate urea with an organic acid cocatalytically to promote insertion reaction with aryldiazoacetates. These reactions are proposed to occur through a HBD induced heteroatom acidity amplification, facilitating protonation of the a-aryldiazoacetates, which can undergo a nucleophilic attack by the conjugate base. Understanding of the insertion mechanism has led to asymmetric cocatalytic variations of the insertion reactions utilizing both chiral acids with achiral HBD catalyst and chiral HBD catalyst with an achiral acid. Work towards an asymmetric reaction has illuminated the one lacking feature of the boronate catalyst: its ability to achieve enantioselectivity, which has been an ongoing problem to advancements with these catalysts. Herein, development of a new chiral catalyst design and a new metal-free approach to a selective insertion reaction are discussed.
Anita Mattson (Advisor)
Claudia Turro (Committee Member)
138 p.
Chemistry; Organic Chemistry
hydrogen bond donor; HBD; catalyst; urea; insertion chemistry; diazo compounds; difluoroboronate urea; organic acid; acid amplification

Recommended Citations

Citations

  • Couch, E. D. (2014). Difluoroboronate Urea-Induced Acid Amplification for Insertion Chemistry [Master's thesis, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1404225572

    APA Style (7th edition)

  • Couch, Erica. Difluoroboronate Urea-Induced Acid Amplification for Insertion Chemistry. 2014. Ohio State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1404225572.

    MLA Style (8th edition)

  • Couch, Erica. "Difluoroboronate Urea-Induced Acid Amplification for Insertion Chemistry." Master's thesis, Ohio State University, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=osu1404225572

    Chicago Manual of Style (17th edition)

osu1404225572
794
© 2014, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.