A Photoflow Reactor for the Continuous Photoredox‐Mediated Synthesis of C‐Glycoamino Acids and C‐Glycolipids

Abstract

Go with the flow: A simple flow reactor has been developed to accommodate highly absorbing [RuL3]2+ photosensitizers for light‐starved photoredox reactions (see picture). The use of vessels having a thin diameter increases the efficiency of the reaction. This methodology has been applied to the divergent synthesis of C‐glycoconjugates.

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

“…It is of note that when the same reaction was carried out employing an excess of KOH as the promoter, 66 was obtained in a much lower yield (69% vs. 97%). In addition, hydration with the Parkins catalyst 1 was also successfully employed to transform the acetate-and pivaloate-protected aminonitrile glycoside 67 and the morphinan derivative 69 into the corresponding primary amides 68 and 70, respectively (Scheme 17) [75,76]. …”

The Development of Visible‐Light Photoredox Catalysis in Flow

“…[4] The design and construction of single-pass, continuous-flow photochemical reactors developed by several groups has allowed for scale-independent photochemical reactors capable of efficiently converting gram and kilogram quantities of material. [5] …”

“…Recently, visible-light photocatalysis has successfully been adapted to flow reactor designs utilized by UV flow photoreactors. [5] In fact, many of the visible-light-induced transformations that have been applied to continuous flow were initially developed as UV-induced batch reactions. Herein, we describe recent applications of continuous-flow chemistry to visible-light photoredox catalysis [6] with an emphasis on advantages over batch reactions as well as an outlook on the influence of flow chemistry for the future development of photochemistry.…”

Design Consideration of Continuous-Flow Photoreactors

“…The assembled reactor was then employed in the visible light photoredox catalyzed conjugate addition of O-protected sugars onto acrolein to form 23, as the first step in the synthesis of different C-glycoaminoacids and C-glycolipids (Figure 1.18). 63 Flow systems could be easily employed for the continuous labscale synthesis of drugs. A photo-Favorskii rearrangement converted an α-chloropropiophenone into ibuprofen in 76% isolated yield in a green medium such as acetone/water (9:1).…”