Kikura T,
Taura Y,
Aramaki Y,
*,
Ooi T.
*
Nagoya University, Japan
p‑Diarylboryl Halothiophenols as Multifunctional Catalysts via Photoactive Intramolecular
Frustrated Lewis Pairs.
J. Am. Chem. Soc. 2024;
146: 20425-20431
DOI:
10.1021/jacs.4c06122
Key words
frustrated Lewis pairs - diarylboryl halothiophenols - photocatalysis - radical–radical
coupling - 1,2-diols - 1,2-aminoalcohols
Significance
The authors describe a new class of p-diarylboryl halothiophenols merging photo- and frustrated Lewis pair activation modes.
The unique properties of the catalyst allow efficient assembly of sterically congested
1,2-diols and 1,2-aminoalcohols through radical–radical coupling.
Comment
The present study showcases how a sophisticated design can efficiently combine diverse
catalytic properties even in a simple thiophenol derivative. The method also provide
an elegant alternative to benzoin-type additions as it does not require a stoichiometric
reductant.
