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Palladium Catalyzed Suzuki-Miyaura Cross-Coupling of Axially Chiral Biaryls

Andert, William D
http://rave.ohiolink.edu/etdc/view?acc_num=osu1367536419

Abstract Details

2013, Master of Science, Ohio State University, Chemistry.
Cross-coupling reactions have been of interest to organic chemists much of the past century. It has only been in the last half century that prominent advances have been discovered, all of which take advantage of organometallic chemistry. The most widely explored reactions use palladium or nickel complexes to promote the cross-coupling of a wide variety of functionalized aryl groups. One such reaction is the Suzuki-Miyaura cross-coupling, which is a transition-metal mediated coupling of an organohalide and an organoborane. As a carbon-carbon bond forming reaction, the Suzuki-Miyaura cross-coupling has great potential in synthetic applications due to its mild conditions and functional group tolerance. An important aspect of the reaction is the ability to impart specific configurations during the formation of new carbon-carbon bonds. Such selectivity has been thoroughly explored in the Suzuki-Miyaura cross-coupling of sp2-sp2 carbon-carbon bonds with the retention of E or Z stereochemistry. However, the formation of axially chiral biaryls still presents an ongoing challenge. Biaryls containing at least three substituents ortho to the aryl-aryl bond exhibit atropisomerism, which gives rise to axial chirality. Thus, the application of asymmetric catalysis to the formation of axial chiral biaryls was of interest. The work presented in this thesis investigates the synthesis of several chiral ligands for use in cross-coupling reactions and a study of the Suzuki-Miyaura cross-coupling of biaryls.
T. V. RajanBabu (Advisor)
Jon Parquette (Committee Member)
Chemistry; Organic Chemistry

Recommended Citations

Citations

  • Andert, W. D. (2013). Palladium Catalyzed Suzuki-Miyaura Cross-Coupling of Axially Chiral Biaryls [Master's thesis, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1367536419

    APA Style (7th edition)

  • Andert, William. Palladium Catalyzed Suzuki-Miyaura Cross-Coupling of Axially Chiral Biaryls. 2013. Ohio State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1367536419.

    MLA Style (8th edition)

  • Andert, William. "Palladium Catalyzed Suzuki-Miyaura Cross-Coupling of Axially Chiral Biaryls." Master's thesis, Ohio State University, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=osu1367536419

    Chicago Manual of Style (17th edition)

osu1367536419
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© 2013, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.