Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst

Markushyna Y, Schüßlbauer C, Ullrich T, Guldi DM, Antonietti M, Savateev A (2021)

Publication Type: Journal article

Publication year: 2021

Journal

Angewandte Chemie International Edition Wiley

DOI: 10.1002/anie.202106183

Abstract

Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one-light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.

Authors with CRIS profile

Christoph Schüßlbauer Lehrstuhl für Physikalische Chemie I Tobias Ullrich Lehrstuhl für Physikalische Chemie I Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Max-Planck-Institut für Kolloid- und Grenzflächenforschung / Max Planck Institute of Colloids and Interfaces DE Germany (DE)

How to cite

APA:

Markushyna, Y., Schüßlbauer, C., Ullrich, T., Guldi, D.M., Antonietti, M., & Savateev, A. (2021). Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst. Angewandte Chemie International Edition. https://dx.doi.org/10.1002/anie.202106183

MLA:

Markushyna, Yevheniia, et al. "Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst." Angewandte Chemie International Edition (2021).

BibTeX: Download