(509am) Paired Electrochemistry: Radical Lifetime Control Under Microfluidic Devices

Electroorganic synthesis has recently emerged as a powerful tool to activate the redox chemistry in place of conventional oxidants or reductants. It offers opportunities to promote single-electron transfer (SET) redox-neutral chemistries similar to those recently discovered using visible-light photocatalysis but without the use of an expensive photocatalyst. In this talk, we introduce a microfluidic redox-neutral electrochemistry (µRN-eChem) platform that is able to selectively couple highly reactive intermediates generated on two separate electrodes. The cathode and anode simultaneously generate the corresponding reactive intermediates, and selective transformation is facilitated by the rapid molecular diffusion across a microfluidic channel that outpaces the decomposition of the intermediates. This platform was demonstrated to have broad applicability to SET chemistry, including radical-radical cross-coupling, Minisci-type reactions, and nickel-catalyzed C(sp²)–O cross-coupling. In addition, µRN-eChem was shown to enable a two-step gram-scale electrosynthesis of a nematic liquid crystal compound to demonstrate its practicality.