Angled Vortex Fluidic Mediated Multicomponent Photocatalytic and Transition Metal‐Catalyzed Reactions

Abstract

The dynamic thin film formed in an angled rapidly rotating tube in a vortex fluidic device (VFD) is effective in facilitating multicomponent reactions (MCRs) as photocatalytic or metal-mediated processes. Here, we demonstrate the utility of the VFD by using two known MCRs, an Ugi-type three component reaction and an A -coupling reaction. The Ugi-type reaction can be done in either confined or continuous-flow modes of operation of the microfluidic platform whereas the A -coupling reaction was optimized for the confined mode of operation. The examples tested gave excellent yields with short reaction times.

Visible-light photocatalytic metal-free multicomponent Ugi-like chemistry

“…It is worth noting that the possibility to harness the photocatalytic activity of isocyanides under irradiation with visible light enabled to avoid the use of additional oxidants such as benzoyl peroxide 20 and DEAD 21 as well as the use of photocatalysts such as either ruthenium- or iridium-based polypyridyl complexes 22 or organic dyes. 23 Furthermore, a two-step-one-pot Ugi-like 3CR (UC-3CR-2S), using 2,4-dimethoxybenzyl isocyanide as a cleavable one, afforded linear non-cyclic secondary imides. To our knowledge, such isocyanide was reported herein as a cleavable one for the first time and proved to be superior to other well-known isocyanides that are able to release a C- or a CN-unit.…”

“…35-7.34 (m, 1H), 7.31-7.28 (m, 3H), 7.27-7.22 (m, 4H), 7.21-7.18 (m, 1H), 7.16-7.13 (m, 4H), 7.10-7.07 (m, 3H), 7.03-7.02 (m, 4H), 6.99-6.96 (m, 4H), 6.86 (t, J = 7.2 Hz, 1H), 6.81 (t, J = 7.2 Hz, 1H), 6.24-6.23 (m, 2H), 3.86 (q, J = 6.7 Hz, 1H), 3.82 (q, J = 6.8 Hz, 1H), 3.75-3.71 (m, 1H), 3.70-3.67 (m, 1H), 3.64-3.50 (m, 4H), 3.04-3.00 (m, 1H), 2.97-2.85 (m, 3H), 2.45-2.43 (m, 4H), 1.93-1.87 (m, 1H), 1.86-1.80 (m, 2H), 1.75-1.68 (m, 2H), 1.63-1.61 (m, 2H), 1.51 (d, J = 6.8 Hz, 3H), 1.41-1.36 (m, 8H), 1.05-0.99 (m, 2H), 0.95-0.89 (m, 4H), 0.88-0.86 (m, 12H), 0.76-0.74 (m, 2H), 0.64-0.58 (m, 1H), 0.53-0.51 (m, 1H); 13 C NMR (176 MHz, CDCl 3 ) δ 178. 8, 178.0, 177.7, 149.2, 148.7, 140.7, 140.7, 137.8, 137.6, 135.7, 135.4, 132.9, 132.3, 129.6, 129.5, 129.3, 129.3, 128.4, 128.4, 127.9, 127.8, 127.8, 127.6, 127.4, 127.3, 126.3, 126.3, 119.2, 118.8, 115.7, 115.1, 63.5, 63.5, 58.9, 58.5, 46.7, 46.6, 45.0, 45.0, 30.9, 30.4, 30.2, 29.7, 29.4, 27.8, 27.2, 26.6, 26.6, 26.3, 26.3, 25.0, 22.3, 22.3, 20.5, 20.2 (23). The crude material (reaction time: 72 h) was purified by column chromatography (n-hexane/ethyl acetate 98.5 : 1.5) to give the product as an orange amorphous solid (31.9 mg, 87% yield).…”

“…By applying standard conditions as for the Ugi-3CR (Table 1, entry 2) a small library of imide derivatives (20)(21)(22)(23)(24)(25)Fig. 3) was obtained.…”

Three-step-in-one synthesis of supercapacitor MWCNT superparamagnetic magnetite composite material under flow

“…This dual eld effect application of the VFD adds to the versatility of the device, extending its eld effect capabilities, with others including plasma processing and continuous light sources. 73,74 The generation of Fe 3 O 4 @MWCNT directly from pristine MWCNTs avoids the use of harsh chemicals while dramatically reducing the processing time, all of which are important in developing any applications. To this end, we have demonstrated the utility of the composite material retained in the VFD tube, in a high performing supercapacitor.…”

Inorganic–organic hybrid materials to detect urinary biomarkers: recent progress and future prospects

“…Vortex fluid device (VFD) is a successful example of a rotating reactor system. 158,159 With the support of the VFD, several chemical reactions happen more quickly or generate much greater yields, including amide coupling, 160 photoredox reactions 161 and azide-alkyne cycloaddition. 162 VFD is useful in a number of procedures in inorganic-organic material production, and it has been claimed that decorating carbon nanoonions with platinum or palladium nanoparticles, 163 or combining VFD with a pulsed laser, can successfully create metal nanoparticles and magnetite composites.…”