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An Under-Appreciated Source of Reproducibility Issues in Cross-Coupling: Solid-State Decomposition of Primary Sodium Alkoxides in Air

preprint
submitted on 17.08.2020 and posted on 19.08.2020 by Robert Wethman, Joseph Derosa, Van Tran, Taeho Kang, Omar Apolinar, Anuji Abraham, Roman Kleinmans, Steven Wisniewski, John Coombs, Keary Engle
The decomposition of primary sodium alkoxide salts under ambient storage conditions and the effects of this phenomenon on commonly employed transition-metal-catalyzed cross-coupling reactions are described. By utilizing NMR, IR, and Raman spectroscopy, along with a modified Karl Fischer analysis, the main inorganic degradants were characterized, and CO2 in the air was found to be a critical reactant within the decomposition process. The effects of storage conditions on decomposition were evaluated, and the preliminary experiments to understand the kinetics of this process were performed.

Funding

NSF-CHE-1800280

NSF-DGE-1346837

NSF-DGE-1842471

Kwanjeong Educational Foundation

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

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