Micellar Catalysis Using a Photochromic Surfactant: Application to the Pd-Catalyzed Tsuji–Trost Reaction in Water

Abstract

The first example of a Pd-catalyzed Tsuji-Trost reaction, applied in a photochromic micellar media under conventional heating and microwave irradiation, is reported. The surfactant activity and recycling ability were investigated and compared with those of a few commercially available surfactants. The synthetic photochromic surfactant proved to be efficient, recyclable, and versatile for Pd-catalyzed coupling reactions.

Reversible pH‐ and Photocontrollable Carbohydrate‐Based Surfactants

“…Small-angle neutron scattering spectra demonstrate the wide range of aggregate morphologies and aggregation numbers for the surfactants, showing how subtle molecular design of the head-group size and stereochemistry can control aggre- gation (Figure 2). Model fits to the experimental SANS data (shown as solid lines in Figure 2) indicate that the anionic glucuronic acid-based surfactants GlcU-Azo (7) and GlcU-Tz-Azo (8) exhibit relatively small, oblate spheroidal and squat cylindrical micelles, respectively. As expected from previous studies of structure-function relationships [24] for uronic acid-derived surfactants, [20] the anionic form produces significantly smaller micelles than the protonated, non-ionic variants.…”

“…[4] By far the most widely used photo-isomerizable chromophore is the robust and wellcharacterized azobenzene moiety, which provides the additional benefit of a tendency to self-assemble into liquid crystalline phases. [5] Photo-isomierizable amphiphiles have found potentially powerful applications in fields as diverse as synthesis and catalysis, [6][7][8] gene expression, [9] DNA [10] and protein aggregation, [11] drug delivery, [12] oil/water separation, [13] switchable vesicles [14] and controlled gelation. [15] Pivotal to these applications is the capacity to design and access structural motifs targeted for function.…”

“…To develop an understanding of the properties of these surfactants, studies commenced with the modular assembly of eight surfactants (1)(2)(3)(4)(5)(6)(7)(8), which possess a variable mono-and disaccharide head-group linked to a butylazobenzene moiety through a triethylene glycol spacer, with and without a triazole linker. This was achieved using the well-established CuAAc reaction and Lewis-acid promoted glycosylation, respectively (see the Supporting Information for synthetic details).…”

Micellization and Single-Particle Encapsulation with Dimethylammoniopropyl Sulfobetaines

“…1,2 Such micelles are ubiquitous in soaps and detergents, and have also drawn attention as nanosized capsules for dyes, 3 drugs, 4 and inorganic nanoparticles (NPs), 5−8 and as catalyst supports in aqueous solution, wherein the biphasic interface is confined to volumes of a few nanometers. 9,10 …”

Synthesis of substituted allyl acetates from heterocyclic dienes by Pd-promoted arylation-acetoxylation cascade

“…[6][7][8][9][10][11][12][13] Amongst them, Pd-catalysed processes stand as the most intensively studied methodologies frequently used in the synthesis of various organic molecules, including naturally occurring substances. [14][15][16][17][18][19][20][21][22] The most common way to access allylic acetates utilizes allyl alcohols as starting materials, which are widely accessible via addition of vinyl-nucleophiles on aldehydes or ketones or simple nucleophilic additions on α,β-unsaturated equivalents. [23][24][25][26] Some alternative processes usually based on the acetoxylation of alkenes or related compounds have also been developed.…”