Kinetic Study of Carbophilic Lewis Acid Catalyzed Oxyboration and the Noninnocent Role of Sodium Chloride.

ABSTRACT: In the present study, the oxyboration reaction catalyzed by IPrAuTFA in the presence and absence of NaTFA has been examined with kinetic studies, mass spectrometry, and ¹H NMR and ¹¹B NMR spectroscopy. Data from monitoring the reactions over the temperature range from 30 to 70 °C, the catalyst range from 1.3 to 7.5 mol %, and the NaTFA additive range from 2.5 to 30 mol % suggests a mechanism that involves rate-determining catalyst generation. Data from additive studies that replaced NaTFA with NaBARF (BARF = tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) or Bu₄NTFA as an alternative additive suggest that catalyst quenching from residual NaCl remaining from a one-pot substrate synthesis/reaction method is the cause of this effect, despite the low solubility

SUBMITTER: Johnson JS 

PROVIDER: S-EPMC6474369 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature