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Updated: Nov 2, 2025

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
Published on: February 20, 2020
Exploiting single-electron transfer in Lewis pairs for catalytic bond-forming reactions
Yoshitaka Aramaki1, Naoki Imaizumi1, Mao Hotta1
1Institute of Transformative Bio-Molecules (WPI-ITbM), Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University Nagoya 464-8601 Japan tooi@chembio.nagoya-u.ac.jp.
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.
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