Issue 9, 2023

Rapid access to polycyclic thiopyrylium compounds from unfunctionalized aromatics by thia-APEX reaction

Abstract

We developed a sulfur-embedding annulative π-extension (thia-APEX) reaction that could construct a sulfur-embedding cationic hexagonal aromatic ring, thiopyrylium, onto unfunctionalized aromatics in one step. The key of thia-APEX is the use of S-imidated ortho-arenoyl arenethiols, and a variety of π-extended thiopyryliums can easily be synthesized. The synthesized thiopyryliums showed diverse absorption and emission properties over the visible light to NIR region, depending on minor structural differences.

Graphical abstract: Rapid access to polycyclic thiopyrylium compounds from unfunctionalized aromatics by thia-APEX reaction

Supplementary files

Article information

Article type
Communication
Submitted
02 Nov 2022
Accepted
20 Dec 2022
First published
20 Dec 2022

Chem. Commun., 2023,59, 1157-1160

Author version available

Rapid access to polycyclic thiopyrylium compounds from unfunctionalized aromatics by thia-APEX reaction

K. P. Kawahara, H. Ito and K. Itami, Chem. Commun., 2023, 59, 1157 DOI: 10.1039/D2CC06706D

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