Efficient catalysis in dynamic nanomicelles of PS-750-M suspended in water

Trichloromethyl Carbanion in Aqueous Micelles: Mechanistic Insights and Access to Carboxylic Acids from (Hetero)aryl Halides

“…Aryl bromides bearing active methyl (13,25) or methylene (14, 19) groups afford the corresponding acids without unwanted α-arylated byproducts. Substrates containing other important functional groups, such as nitriles (19,34), ethers (8,24,26,33,35,37), trifluoromethyl (6,7,24), tert-amine (10), and carbamate (15) exhibited good reactivity. Although the reaction based on the conversion as determined by in-process NMR analysis was good-to-excellent, the isolated yield of the substrate containing dibenzyl amine (10) was poor.…”

“…Using water as a reaction media presents a number of environmental benefits compared to traditional organic solvents. − Over the last 10 years, great strides have been made using designer surfactants to generate aqueous micelles where a myriad of organic transformations efficiently occur. − However, perhaps even more exciting chemistry includes the novel and sometimes complimentary reactivity offered inside these self-assembled micelles. We have been particularly interested in exploiting the unique environment found within micelles to stabilize otherwise highly reactive species to harness their use in transition-metal catalysis. − Due to the possibility of stabilization of extremely sensitive intermediates under the protecting environment of micelles, − we studied trichloromethyl carbanion and its stability toward decomposition.…”

The E factor at 30: a passion for pollution prevention

“…Interestingly, Handa and co-workers 54 recently designed a proline-based amphiphile, PS-750-M (Scheme 3), containing a tertiary amide function. Their goal was to replace polar aprotic solvents such as DMF and NMP through the formation of designer nanoreactors.…”

Rapid Amide Coupling in Water for Undergraduate Laboratories

“…As our research group is dedicated to sustainable organic synthesis and catalysis, we decided to incorporate a new experiment into the present curriculum of the teaching lab at the University of Louisville covering the various aspects of sustainable chemistry. The main aim of designing an experiment was to acquaint students with sustainability (organic-solvent-free reactions) and the harmful impacts of solvents; this aim is aligned with the fifth principle of green chemistry, which promotes the use of benign solvents and auxiliaries. , Toward this goal, our group has developed a proline-based environmentally benign amphiphile, PS-750-M, that enables organic transformations in water. , Here, the word amphiphile means a molecule possessing both hydrophilic and hydrophobic components in a balanced ratio. This amphiphile has an optimal balance between the hydrophilic mPEG chain and the hydrophobic hydrocarbon region.…”