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Design of highly efficient organic photocatalysts for visible-light driven reductive dehalogenation of aryl halides

Abstract

Department of Materials Science and EngineeringAbstracting halide ions from organohalide compounds and generating free-radical to produce reactive intermediate have proven to be very important and useful step in chemical synthesis and have also found numerous applications in the synthesis procedures. Hence, many scientists have thrived to improve and promote this dehalogenation process to more efficient, simple, and environmentally friendly way. Adoption of photocatalytic way, the conversion of light energy into chemical energy, was the most prominent of all, as it is the inexpensive and sustainable way to induce chemical reactions. It is widely known to utilize inorganic photocatalysts such as iridium or ruthenium complex catalysts with high concentration relative to substrate in dehalogenation. However, their hazards and toxicity were of great concerns, thus many researches were done to make use of organic photocatalysts. Still there have been many problems such as involving UV region for the activation of catalysts, requisites for harsh condition, high catalyst loading or difficulties in reducing chloro- or electron rich bromo aryls. So here in we present purely organic photocatalyst designed to attain sufficient triplet lifetime to achieve visible light mediated single electron transfer process (SET). It successfully demonstrates facile dehalogenation in mild condition with most of the aryl halides, even with the chloro- and electron rich bromo aryls which are reported to be difficult to reduce, and also shows remarkable yield with catalyst loading down to sub-ppm level. In addition, oxygen tolerance feature of the catalyst notes that not only singlet state but also triplet state should be taken a close look at.clos

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