Micellar Catalysis as a Tool for C–H Bond Functionalization toward C–C Bond Formation

Abstract

Micelles generated upon dissolving surfactants in water can be employed as nanovessels for catalytic transformations, in the so-called micellar catalysis methodology. This review is focused on the use of micellar catalysis in the context of the catalytic functionalization of carbon−hydrogen bonds. The micelles accumulate catalyst and reactants in their inner volume in such a high local concentration that kinetics are favored. The consequence is that, in most cases, processes that in conventional organic solvents require high temperatures and long reaction times are achieved in milder conditions when micellar catalysis is employed.

On the role of surfactants: rethinking “aqueous” chemistry

“…Whatever the explanation, not only is chemistry in water essential in order to minimize its contribution to climate change; not only is it crucial for preserving and extending the planet's limited supplies of natural resources and minimizing our investment in energy, but it also encourages alternative ways of thinking about doing organic synthesis. Judging from the reviews of late, 12 it sure seems that Nature remains patiently waiting for chemists to continuously discover, apply, and profit from its “secrets”, just by switching to water (Fig. 2).…”

Metal-Free Synthesis of Guanidines from Thioureas in Water Reactions Mediated by Visible Light

“…In recent years, Lipshutz and others have developed surfactant technology for the organic synthetic field. 42 43 44 45 46 Surfactants, also known as surface-active agents, such as nonionic, cationic, and anionic, are composed of hydrophilic and hydrophobic parts that can mediate the interaction of insoluble reactants with water. 47 We also reported the first guanylation in-water reaction, using a stoichiometric amount of diacetoxyiodobenzene as a desulfurizing agent and TPGS-750-M as a surfactant.…”

“…Even though on water reactions are considered green media, the heterogeneous system causes the limitations of some substrates and catalysts due to the solubility. In recent years, Lipshutz and others developed surfactant technology for organic synthetic field [42][43][44][45][46] . Surfactants, also known as surfaceactive agents, such as non-ionic, cationic, and anionic, are composed of hydrophilic and hydrophobic parts that can mediate the interaction of insoluble reactants with water 47 .…”

An efficient mixed micellar strategy for the catalytic oxidation of benzyl alcohol by diperiodatoargentate(iii) in aqueous media

“…[3][4][5] Hence, synthetic organic chemists prefer to use surfactant solutions to carry out a wide variety of organic reactions in completely green media such as water. [6][7][8][9][10] The micellar strategy brings steps toward green synthesis closer to mitigate the negative effects on the environment caused by the extensive use of volatile organic solvents. 11,12 A single surfactant producing a micellar microenvironment was established as the finest reaction medium, yet a mixed micellar system formulated with multiple surfactants appeared to be one of the best alternatives.…”