Expansion of the iterative cross-coupling synthesis strategy through Csp3 halide cross-coupling, Mida boronate synthesis, and chan-lam couplings
Klubnick, Jenna A.
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https://hdl.handle.net/2142/26352
Description
Title
Expansion of the iterative cross-coupling synthesis strategy through Csp3 halide cross-coupling, Mida boronate synthesis, and chan-lam couplings
Author(s)
Klubnick, Jenna A.
Issue Date
2011-08-26T15:24:32Z
Director of Research (if dissertation) or Advisor (if thesis)
Burke, Martin D.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
M.S.
Degree Level
Thesis
Keyword(s)
methyliminodiacetic acid (MIDA) boronates
organic synthesis
synthetic methods
Suzuki-Miyaura
Chan-Lam
iterative cross-coupling
Csp3-halide
Abstract
The iterative cross-coupling strategy for small molecule synthesis has been shown to be a powerful and effective method for the synthesis of small molecules. However, this strategy was limited by current methodological limitations. Therefore, we have extended the power and application of the iterative cross-coupling strategy by the development of several new methods compatible with the iterative cross-coupling platform. We report a mild Csp3 halide – Csp2boronic acid Suzuki-Miyaura cross-coupling method amenable to fine molecule synthesis. We also report a new method for the synthesis of MIDA boronates which are sensitive to current methods. Finally, we report the extension of the entire iterative cross coupling platform to the Chan-Lam coupling to form carbon-heteroatom bonds.
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