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Tetrahedron Letters 57, 2016, 2059–2062
Mohammad Parvez Alam, Barbara Jagodzinska, Jesus Campagna, Patricia Spilman, Varghese John
Drug Discovery Laboratory, Department of Neurology, University of California, United States
Using the Syrris Asia system researchers at the Dept. of Neurology (University of California, US), have reported high yielding SNAr substitutions of Heteroaryl chlorides to form C-O bonds in microfluidic reactors. In traditional batch conditions, these compounds exhibit low reactivity and are slow even when using metal catalysis. The study demonstrates, under flow conditions, a highly facile C-O bond formation of electron deficient pyrimidines and pyridines with cleaner reaction profiles, high yields, quick scalability and no need for transition metal catalyst. This greener methodology will allow for more rapid and efficient synthesis of key intermediates of industrial importance in a safe and continuous manner.
Abstract: This study describes our development of a novel and efficient procedure for CAO bond formation under mild conditions, for coupling heteroaryl chlorides with phenols or primary aliphatic alcohols. We utilized a continuous-flow microfluidic reactor for C-O bond formation in electron-deficient pyrimidines and pyridines in a much more facile manner with a cleaner reaction profile, high yield, quick scalability, and without the need for the transition metal catalyst. This approach can be of general utility to make CAO bond containing intermediates of industrial importance in a continuous and safe manner.
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