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11.1.1 C(sp2)–C(sp3) Coupling Using Potassium Organotrifluoroborates and Aryl Electrophiles

DOI: 10.1055/sos-SD-229-00192

Kelly, C. B.; Matsui, J. K.; Phelan, J. P.; Gutiérrez Bonet, Á.; Lang, S. B.; Molander, G. A.Science of Synthesis: Photocatalysis in Organic Synthesis, (20181341.

Because of their bench stability, commercial availability, and favorable redox potentials, seminal work in the development of nickel/photoredox dual catalysis employed alkyltrifluoroborates[‌12‌] as latent radicals. Beyond the early work of benzylic cross couplings, secondary,[‌13‌] α-alkoxy,[‌14‌] α-amino,[‌15‌] and tertiary[‌16‌] C(sp2)C(sp3) bond formations using alkyltrifluoroborates have been achieved, providing new CC bond disconnections that were previously challenging under two-electron manifolds. Common electrophilic partners include aryl halides,[‌7‌,‌13‌‌16‌] acyl chlorides,[‌17‌,‌18‌] and in-situ-activated carboxylic acids.[‌19‌] Although iridium-based photocatalysts are typically used, recent reports outline the use of organophotocatalysts to accomplish similar chemistry, increasing the practical application and sustainability of the processes.