The impact of varying percentages of an organic solvent added to reactions run in aqueous nanomicelles as the reaction medium has been investigated. Issues such as rates of reaction, percent conversion, and yield, as well as various practical aspects (e.g., effect on stirring, etc.), are discussed, leading to an operationally simple method for the general improvement of potentially problematic systems across a broad range of reaction types, in particular for reactions run at scale.
An especially mild, safe, efficient, and environmentally responsible reduction of aromatic and heteroaromatic nitro-group-containing educts is reported that utilizes very inexpensive carbonyl iron powder (CIP), a highly active commercial grade of iron powder. These reductions are conducted in the presence of nanomicelles composed of TPGS-750-M in water, a recyclable aqueous micellar reaction medium. This new technology also shows broad scope and scalability and presents opportunities for multistep one-pot sequences involving this reducing agent.
Two
examples of SNAr reactions, each run in the absence
of typically utilized dipolar aprotic solvents (e.g., DMF), have been
scaled to ∼10 g. These are suggestive of the potential for
micellar catalysis in water enabled by a commercially available designer
surfactant (TPGS-750-M) to serve as a replacement for traditionally
employed organic solvents.
Several types of reduction reactions in organic synthesis are performed under aqueous micellar‐catalysis conditions (in water at ambient temperature), which produce a significant volume of foam owing to the combination of the surfactant and the presence of gas evolution. The newly engineered surfactant “Coolade” minimizes this important technical issue owing to its low‐foaming properties. Coolade is the latest in a series of designer surfactants specifically tailored to enable organic synthesis in water. This study reports the synthesis of this new surfactant along with its applications to gas‐involving reactions.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.