Showing papers by "Glenn M. Sammis published in 2022"
TL;DR: It is demonstrated that the scope of thionyl fluoride-mediated one-pot reactions can be extended beyond nucleophilic acyl substitutions to mild reductions of carboxylic acids using NaBH4.
Abstract: Thionyl fluoride (SOF2) is an underutilized reagent that is yet to be extensively studied for its synthetic applications. We previously reported that it is a powerful reagent for both the rapid syntheses of acyl fluorides and for one-pot peptide couplings, but the full scope of these nucleophilic acyl substitutions had not been explored. Herein, we report one-pot thionyl fluoride-mediated syntheses of peptides and amides (35 examples, 45-99% yields) that were not explored in our previous study. The scope of thionyl fluoride-mediated nucleophilic acyl substitutions was also expanded to encompass esters (24 examples, 64-99% yields) and thioesters (11 examples, 24-96% yields). In addition, we demonstrate that the scope of thionyl fluoride-mediated one-pot reactions can be extended beyond nucleophilic acyl substitutions to mild reductions of carboxylic acids using NaBH4 (13 examples, 33-80% yields).
6 citations
TL;DR: In this paper , the authors demonstrate two complementary strategies for the syntheses of sulfonyl fluorides using sulfonic acids and their salts, using Xtalfluor-E® as a bench stable solid.
3 citations
TL;DR: In this article , an electrochemical-based method was proposed to detect fentanyl at <10 ppb (<30 nM) with a limit of detection of 2 ppb and a calibration curve that covered 4 orders of concentration (from 1 ppb to 10 ppm).
Abstract: The opioid overdose crisis in North America worsened during the COVID-19 pandemic, with multiple jurisdictions reporting more deaths per day due to the fentanyl-contaminated drug supply than COVID-19. The rapid quantitative detection of fentanyl in the illicit opioid drug supply or in bodily fluids at biologically relevant concentrations (i.e., <80 nM) remains a significant challenge. Electroanalytical techniques are inexpensive and can be used to rapidly detect fentanyl, but detection limits need to be improved. Herein, we detail the development of an electrochemical-based fentanyl analytical detection strategy that used a glassy carbon electrode modified with electrochemically reduced graphene oxide (ERGO) via electrophoretic deposition. The resulting surface was further electrochemically reduced in the presence of fentanyl to enhance the sensitivity. Multiple ERGO thicknesses were prepared in order to prove the versatility and ability to fine-tune the layer to the desired response. Fentanyl was detected at <10 ppb (<30 nM) with a limit of detection of 2 ppb and a calibration curve that covered 4 orders of concentration (from 1 ppb to 10 ppm). This method was sensitive to fentanyl analogues such as carfentanil. Interference from the presence of 100-fold excess of other opioids (heroin, cocaine) or substances typically found in illicit drug samples (e.g. caffeine and sucrose) was not significant.
1 citations