Developing flow photo-thiol–ene functionalizations of cinchona alkaloids with an autonomous self-optimizing flow reactor

Abstract

Continuous flow photo-thiol-ene reactions on cinchona alkaloids with a variety of organic thiols have been developed to deliver a series of unprecedented architectures. A self-optimizing flow photochemical reactor was deployed...

Synthesis of Thiomorpholine via a Telescoped Photochemical Thiol–Ene/Cyclization Sequence in Continuous Flow

“…Therefore, it appeared advantageous to employ a photocatalyst, a common practice for this photochemical reaction. For thiol–ene reactions in continuous flow, 2,2-dimethoxy-2-phenylacetophenone (DMPA) as a photoinitiator or Ru­(bpy) 3 (PF 6 ) 2 as a photocatalyst have been reported. − While Ru­(bpz) 3 (PF 6 ) 2 has been reported to catalyze the thiol–ene reaction of similar thiol substrates such as cysteine methyl ester via a single electron transfer mechanism, it was important to avoid expensive metal catalysts in our approach. Therefore, to accelerate this reaction, we envisioned employing 9-fluorenone (9-FL) as an inexpensive photocatalyst .…”

Autonomous model-based experimental design for rapid reaction development

“…Particularly for photochemical reactions, there has been relatively little investigation into the influence of light intensity and temperature, or the potential interaction effects between these two factors. 31…”

Synthesis of Thiomorpholine via a Telescoped Photochemical Thiol-ene/Cyclization Sequence in Continuous Flow

“…For thiol-ene reactions in continuous flow, 2,2-dimethoxy-2-phenylacetophenone (DMPA) as photoinitiator or Ru(bpy)3(PF6)2 as photocatalyst have been reported. [26][27][28] While Ru(bpz)3(PF6)2 has been reported to catalyze the thiol-ene reaction of similar thiol substrates such as cysteine methyl ester via a single electron transfer (SET) mechanism, 29 it was important to avoid expensive metal catalysts in our approach. Therefore, to accelerate this reaction, we envisioned employing 9-fluorenone (9-FL) as inexpensive photocatalyst.…”