Abstract.We describe the use of visible light in conjunction with an organic dye for the synthesis of phosphoramidates. Cross dehydrogenative coupling reactions between phosphites and amines are reported using organic dyes and light as catalysts for the first time. It is not only a novel application of organic dyes but also fulfils the requirement of sustainability and green chemistry avoiding the use of chromatographic purification technique. The product was simply isolated from the reaction mixture via acid-base workup procedure, rendering the pure product in good yields.
Recently green chemistry has attracted much attention from organic chemists due the problems that our society faces in terms of waste generation and energy consumption. For this reason cross dehydrogenative couplings (CDC) have emerged as one of the most important strategies for C−C bond formation nowadays. In our research group, enticed by the use of organocatalytic cross dehydrogenative coupling reactions and in the synthesis of fluorinated compounds, we developed a new organocatalytic methodology based on the CDC activation of tetrahydroisoquinolines followed by addition of fluoromalonates. The reaction is simply catalyzed by organic dyes (Rose Bengal) using green LED as a light source and oxygen as stoichiometric oxidant and let us to obtain the final fluorinated compounds in good yields.
This work summarizes the electrochemical response of flavanone carbon composite electrodes in comparison with Nafion ® -coated flavanone carbon composite electrodes, for use as voltammetric pH sensors in both buffered and low-buffered media. Square wave voltammetric measurements suggest the peak potential achieved from the electrochemical polymerization after the electron-proton oxidation responds with accuracy to buffered pH solutions for both coated and non-coated electrodes, with a potential shift of 55.1 mV and 54.6 mV per pH unit respectively. However, a considerable improvement in stability, accuracy and sensitivity is provided by the proton-transfer Nafion ® layer in CO 2 bubbled sea water. Furthermore, Nafion ® -coated flavanone carbon composite electrodes predicted a pH of 8.04 for the commercial seawater, which is in excellent agreement with the measured pH 8.05 value.
Organophotocatalytic Synthesis of Phosphoramidates. -Dehydrogenative cross--coupling reactions between phosphites and amines are performed using organic dyes and visible light, thus providing a sustainable and green protocol for preparation of phosphoramidates. The reaction is restricted to diethyl phosphite. -(MEAZZA, M.; KOWALCZUK, A.; SHIRLEY, L.; YANG, J. W.; GUO*, H.; RIOS, R.; Adv. Synth. Catal. 358 (2016) 5, 719-723, http://dx.
A new methodology for the synthesis of fluorinated compounds based on the organo catalytic cross dehydrogenative coupling of tetrahydroisoquinolines with fluoromalonates is developed.
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.