Sodium Ethoxide

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

“…Metal alkoxide salts are widely used bases in organic synthesis . Sodium salts derived from primary alcohols (i.e., NaOMe and NaOEt) are among the simplest, most ubiquitous, and most commonly employed . In particular, they find widespread use in Suzuki–Miyaura cross-couplings and related methods that constitute core synthetic technology in academia and industry (Figure A) .…”