A mild Ru/Ni dual-catalytic desulfinative photoredox Csp2-Csp3 cross-coupling reaction of alkyl sulfinate salts with aryl halides has been developed. The optimized catalyst system, consisting of Ru(bpy)3Cl2, Ni(COD)2 and DBU, smoothly mediates the coupling of a diverse set of secondary and primary non-activated alkyl sulfinate salts with a broad range of electron-deficient aryl bromides, electron-rich aryl iodides and heteroaryl bromides under irradiation with blue light. The procedure is ideal for late-stage introduction of alkyl groups on pharmaceutical intermediates and the Csp2-Csp3 cross-coupling reaction allowed the rapid synthesis of caseine kinase 1δ inhibitor analogues via a parallel medicinal chemistry effort.

Development of a Ru/Ni dual catalytic desulfinative photoredox Csp2-Csp3 cross-coupling

255th National Meeting (2018)

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