2‐Fluoro‐5‐nitrophenyldiazonium: A Novel Sanger‐Type Reagent for the Versatile Functionalization of Alcohols

Abstract

Scheme1.Functionalization strategies based on Sanger-type reagents bearing afreeorp rotectedd iazonium unit.

Development of a continuous flow synthesis of FGIN-1-27 enabled by in-line 19F NMR analyses and optimization algorithms

“…The strong electronwithdrawing properties of the diazonium function strongly activates the aromatic ring toward the nucleophilic attack of MeOH which likely proceeds through a standard additionelimination mechanism. [25][26][27] After 60 minutes of residence time at 60 °C, the targeted diazonium salt 2 almost completely disappeared in favor of the unwanted diazonium salt 5.…”

Visible‐light‐mediated synthesis of 3‐arylsulfonylated thioflavones using an in situ activation strategy

“…With the aim of achieving a gentle and direct synthesis, we envisioned the formation of 3‐arylsulfonylated thioflavones by directly reacting methylthiolated alkynones and aryl amines, employing a surrogate for sulfur dioxide. We envisaged that aryl diazonium salts could be generated in situ during the reaction from aryl amines in the presence of tert ‐butylnitrite and boron trifluoride diethyl etherate 11 . In our previous study, we reported the catalyst‐free, one‐pot synthesis of 3‐arylsulfonylated thioflavones using DABSO as a sulfur dioxide surrogate 7 .…”

“…We envisaged that aryl diazonium salts could be generated in situ during the reaction from aryl amines in the presence of tert-butylnitrite and boron trifluoride diethyl etherate. 11 In our previous study, we reported the catalyst-free, one-pot synthesis of 3-arylsulfonylated thioflavones using DABSO as a sulfur dioxide surrogate. 7 Therefore, the reaction was initially carried out without the use of a catalyst.…”