Exploring the influence of designer surfactant hydrophobicity in key C C/C N bond forming reactions

Towards a sustainable tomorrow: advancing green practices in organic chemistry

“…[160][161][162] In response to sustainability imperatives, a new wave of designer surfactants has emerged, [163][164][165][166][167][168] offering promising alternatives and leveraging micellar catalysis to facilitate diverse organic transformations (Scheme 8). [169][170][171][172] Lipshutz's pioneering contributions have significantly advanced the realm of micellar catalysis, mainly through innovative methodologies facilitating the utilization of newly designed PEG-based surfactants across diverse organic transformations, 173 notably in cross-coupling chemistry 126,135,154,172 These surfactants, meticulously crafted to incorporate readily available, non-toxic, and biodegradable components, have garnered widespread acclaim. Among the notable iterations are the first-generation PTS, the second-generation TPGS-750-M, and the third-generation SPGS-550-M, also known as Nok, which have found extensive applications within the Lipshutz group.…”

“…160–162 In response to sustainability imperatives, a new wave of designer surfactants has emerged, 163–168 offering promising alternatives and leveraging micellar catalysis to facilitate diverse organic transformations (Scheme 8). 169–172…”

Recent designer surfactants for catalysis in water

“…Further successful applications of this promising new designer surfactant are the Pd catalyzed cross-coupling Heck reactions reported in Scheme 23. 50 Specifically, SMPS was explored for the transformation of a series of anilines to the corresponding densely substituted biologically relevant skatole derivatives in an aqueous medium via 5-exo-trig cyclization reactions. The scope of the reaction was further extended to intermolecular Csp 2 -Csp 2 and Csp 2 -N bond forming reactions in water.…”

Self‐Assembled Quaternary Ammonium‐Containing Comb‐Like Polyelectrolytes for the Hydrolysis of Organophosphorous Esters: Effect of Head Groups and Counter‐Ions

“…Catalytic acceleration of chemical reactions in surfactant solutions is caused by micelle formation and transfer of reagents and substrates in micellar pseudophase. [16] Catalytic efficacy is determined by optimization of molecular structure (charge and structure of amphiphilic molecule head group and chain length [17][18][19] ), concentration and type of self-assemblies (micelles, rods, vesicles etc.). [20][21][22][23] Cationic surfactants are the most promising due to the charge of head group for biological applications, [3] environmental issues (extractants and flocculants) [24][25][26] and as catalysts in nucleophilic substitution reaction for hydrolysis of ester bonds.…”