Photocatalytic reverse polarity Povarov reaction

“Hepatochem PhotoRedOx Box, equipped with a Kessil 40W LED light. A cardboard cover was also placed over the reactor during reactions. Capable of carrying out up to 8 reactions at one time. Accurate and reproducible results, high throughput.”


A visible light mediated iridium photocatalysed reverse polarity Povarov reaction of aryl imines and electron deficient alkenes is described. Operating via a putative nucleophilic α-amino radical, generated by a proton coupled electron transfer process, addition to a range of conjugated electron deficient alkene substrates affords substituted tetrahydroquinoline products in high yields and with typically good to excellent diastereoselectivity in favor of the trans diastereoisomer. Sub-stoichiometric quantities of Hantzsch ester were found to be key to initiate the overall redox-neutral, free radical cyclization cascade. This new reaction complements existing two electron Lewis acid mediated variants and expands the capabilities of imine umpolung chemistry to synthetically relevant cyclisation methodology.



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