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Synthesis 2022; 54(15): 3409-3413
DOI: 10.1055/a-1776-0929
special topic
Bürgenstock Special Section 2021 – Future Stars in Organic Chemistry

Properties and Synthetic Performances of Phenylamino Cyanoarenes under One-Photon Excitation Manifolds

Tommaso Bortolato‡
a   Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy
,
Mateusz Dyguda‡
a   Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy
b   Institute of Organic Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland
,
Alberto Vega-Peñaloza∗
a   Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy
,
Luca Dell’Amico  ∗
a   Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy
› Author AffiliationsUniversità degli Studi di Padova
Università degli Studi di Padova (P-DiSC#11BIRD2020-UNIPD) (L.D.), and Fondazione Cassa di Risparmio di Padova e Rovigo (CaRiPaRo Foundation, Synergy – Progetti di Eccellenza 2018) (L.D.) are acknowledged for financial support.
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In memory of Blas Flores Pérez (1963–2021)

Abstract

The synthesis of a set of new organic photocatalysts (PCs) with a donor-acceptor carbazolyl dicyanobenzene structure is reported. The PCs developed have fine-tailored redox potentials from –1.62 V (PC•+/PC*) to 1.36 V (PC*/PC•–) and were accessed through a straightforward two-step synthesis. The potential of these PCs was demonstrated in synthetically relevant reactions with mechanistically opposite thermodynamic requirements, previously reported only in the presence of precious Ir-based PCs. In addition, the PCs outperformed the yields promoted by the well-established 4CzIPN organic dye in both type of reactions.

Key words

light-driven reactions - photoredox catalysis - organocatalysis - synthetic methods - radical chemistry

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1776-0929. Procedures and characterization data are included.
  • Supporting Information


Publication History

Received: 08 December 2021

Accepted after revision: 18 February 2022

Accepted Manuscript online:
18 February 2022

Article published online:
19 April 2022

© 2022. Thieme. All rights reserved

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