Expanding automated modular small molecule synthesis
Wang, Wesley
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Permalink
https://hdl.handle.net/2142/125745
Description
Title
Expanding automated modular small molecule synthesis
Author(s)
Wang, Wesley
Issue Date
2024-06-06
Director of Research (if dissertation) or Advisor (if thesis)
Burke, Martin D
Doctoral Committee Chair(s)
Burke, Martin D
Committee Member(s)
Denmark, Scott E
Sarlah, David
Schroeder, Charles M
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
TIDA Boronate, Cross-coupling, Iterative, Modular, Automation
Abstract
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.
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