Expanding automated modular small molecule synthesis

Small molecules are incredibly diverse, yet, accessing them is often challenging due to their complexity. Iterative cross-coupling has tremendous potential to simplify the synthesis of small molecules via repetitive connections. Recently, tremendous strides have been made towards the development of better systems for iterative cross-coupling. In this thesis, we discuss how the new TIDA boronate improves and expands accessible iterative cross-coupling space. The increased tolerance of TIDA boronates towards reaction conditions enables compatibility with superior Suzuki cross-coupling reactions that speed up automated small molecule synthesis by 10-fold. In addition, TIDA boronates enable access to previously incompatible Csp3 cross-coupling reactions, allowing for important classes of small molecules to be synthesized iteratively.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2024

Author dc:creator

• Wang, Wesley

Contributors dc:contributor

• Burke, Martin D
• Denmark, Scott E
• Sarlah, David
• Schroeder, Charles M

• Tida Boronate
• Cross-coupling
• Iterative
• Modular
• Automation

Statement dc:rights

• Copyright 2024 Wesley Wang

Language dc:language

en, eng

Handle dc:identifier

https://hdl.handle.net/2142/125745

OAI record oai:identifier

https://www.ideals.illinois.edu/oai-pmh?verb=GetRecord&metadataPrefix=etdms&identifier=oai%3Awww.ideals.illinois.edu%3A2142%2F125745