Exploiting single-electron transfer in Lewis pairs for catalytic bond-forming reactions |
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| Authors: | Yoshitaka Aramaki Naoki Imaizumi Mao Hotta Jun Kumagai Takashi Ooi |
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| Affiliation: | Institute of Transformative Bio-Molecules (WPI-ITbM), Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601 Japan.; Institute of Materials and Systems for Sustainability, Nagoya University, Nagoya 464-8601 Japan ; CREST, Japan Science and Technology Agency (JST), Nagoya University, Nagoya 464-8601 Japan |
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| Abstract: | A single-electron transfer (SET) between tris(pentafluorophenyl)borane (B(C6F5)3) and N,N-dialkylanilines is reported, which is operative via the formation of an electron donor–acceptor (EDA) complex involving π-orbital interactions as a key intermediate under dark conditions or visible-light irradiation depending on the structure of the aniline derivatives. This inherent SET in the Lewis pairs initiates the generation of the corresponding α-aminoalkyl radicals and their additions to electron-deficient olefins, revealing the ability of B(C6F5)3 to act as an effective one-electron redox catalyst.Radical–ion pair generation from common Lewis pairs and its application to catalytic carbon–carbon bond formation. |
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