Photocatalytic denitrative homo-and cross-coupling of nitroalkanes towards the synthesis of alkenes Author Information

Alkenes are essential motifs in natural products and synthetic molecules, but there is still a need for efficient, mild, and versatile olefination methods. Nitroalkanes, known for their wide reactivity as nucleophiles or radicals, still hold untapped potential in photocatalysis. Here, we present a unified, photocatalytic method to generate-nitroalkyl radicals by oxidizing simple, non-prefunctionalized nitronates. These radicals then add to another nitronate and undergo double denitration to produce alkenes (homo-or cross-coupling). This process takes advantage of the dual nucleophilic and electrophilic behavior of nitroalkanes and offers broad functional-group compatibility, challenging the traditional McMurry-type coupling, which cannot tolerate reducible groups. Additionally, this scalable approach demonstrates its usefulness by synthesizing medicinally important compounds like Combretastatin and lignan-type cores.