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Atropoenantioselective palladaelectro-catalyzed anilide C–H olefinations viable with natural sunlight as sustainable power source
Authors:Johanna Frey  Xiaoyan Hou  Lutz Ackermann
Affiliation:Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße, 237077 Göttingen Germany.; Wöhler Research Institute for Sustainable Chemistry, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen Germany
Abstract:
Enantioselective electrocatalyzed transformations represent a major challenge. We herein achieved atropoenantioselective pallada-electrocatalyzed C–H olefinations and C–H allylations with high efficacy and enantioselectivity under exceedingly mild reaction conditions. With (S)-5-oxoproline as the chiral ligand, activated and non-activated olefins were suitable substrates for the electro-C–H activations. Dual catalysis was devised in terms of electro-C–H olefination, along with catalytic hydrogenation. Challenging enantiomerically-enriched chiral anilide scaffolds were thereby obtained with high levels of enantio-control in the absence of toxic and cost-intensive silver salts. The resource-economy of the transformation was even improved by directly employing renewable solar energy.

Asymmetric pallada-electrocatalyzed C–H activation of achiral anilides were accomplished by catalyst control with high levels of enantioselectivity. Dual catalysis was devised, while photovoltaic cells could be used to empower the electrocatalysis.
Keywords:
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