Issue 66, 2023

Light-controlled pKa value of chiral Brønsted acid catalysts in enantioselective aza-Friedel–Crafts reaction

Abstract

Bis(dithienylethene)-based BINOL-derived phosphoric acid (DTE-BPA) has been developed as a light-controlled chiral organocatalyst for the first time. The photoinduced modulation of the reactivity and selectivity via the open/close isomerization of the DTE scaffold led to superior light-controlled ability in the enantioselective aza-Friedel–Crafts reaction of aldimines with indoles. DFT studies showed that photoisomerization is accompanied by a shift of 1.1 pKa units between the open and closed isomers.

Graphical abstract: Light-controlled pKa value of chiral Brønsted acid catalysts in enantioselective aza-Friedel–Crafts reaction

Supplementary files

Article information

Article type
Communication
Submitted
06 Jun 2023
Accepted
20 Jul 2023
First published
21 Jul 2023

Chem. Commun., 2023,59, 9956-9959

Author version available

Light-controlled pKa value of chiral Brønsted acid catalysts in enantioselective aza-Friedel–Crafts reaction

C. G. Krishnan, M. Kondo, O. Yasuda, D. Fan, K. Nakamura, Y. Wakabayashi, H. Sasai and S. Takizawa, Chem. Commun., 2023, 59, 9956 DOI: 10.1039/D3CC02719H

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