Expansion of the iterative cross-coupling synthesis strategy through Csp3 halide cross-coupling, Mida boronate synthesis, and chan-lam couplings

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.

Name thesis:degree_name

M.S.

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Klubnick, Jenna A.

Contributors dc:contributor

• Burke, Martin D.

• methyliminodiacetic acid (MIDA) boronates
• organic synthesis
• synthetic methods
• Suzuki-Miyaura
• Chan-Lam
• iterative cross-coupling
• Csp3-halide

Statement dc:rights

• Copyright 2011 Jenna Klubnick

Language dc:language

en

Handle dc:identifier

http://hdl.handle.net/2142/26352

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/26352