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Thursday, March 30, 2023

In-water Oxidative Suzuki Coupling of Arenes and Arylboronic Acids Utilizing H2O2 as Terminal Oxidant

Suzuki coupling of haloarenes with arylboronic acids is without doubt one of the most necessary C-C bond-forming reactions in natural chemistry. Using arenes as a substitute of pre-functionalized haloarenes for the (oxidative) coupling was believed to be a pretty inexperienced various to the classical Suzuki response. Nevertheless, most oxidative Suzuki reactions have been carried out in natural solvent at excessive temperature, that are operationally harmful [three elements required for combustion: oxidant, heat, and fuel (organic solvent), are unavoidably present] and environmentally unfriendly. Herein, we report a gentle oxidative Suzuki response in water utilizing hydrogen peroxide because the terminal oxidant for the primary time. The elimination of flammable natural solvents from the response prevents potential fires and explosions (ravenous the solvent) whereas the usage of hydrogen peroxide because the oxidant generates no oxidant-derived waste however water as the one byproduct, each of which characterize a big advance from the angle of inexperienced chemistry. By merging our Fenton-bromide system (in water) with Suzuki response (in water), this new formal oxidative Suzuki coupling response was demonstrated with 35 examples and tolerated with many frequent practical teams. As well as, we showcase the extension of this technique to 2 cross-dehydrogenative couplings (oxidative Heck and oxidative Sonogashira), which additional expands the utility of this inexperienced technique in natural synthesis.

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