Photoredox functionalization of C–H bonds adjacent to a nitrogen atom

Abstract

The functionalization of C-H bonds and the visible light photoredox catalysis represent two prominent challenges in organic chemistry. In this regard, the combination of visible-light catalysis and C-H bond functionalization adjacent to a tertiary amine has been successfully developed in the past three years. In this tutorial review, we aim to give a brief overview of this issue and state the main results obtained in the reactions.

The effect of heavy atom to two photon absorption properties and intersystem crossing mechanism in aza-boron-dipyrromethene compounds

“…This component can be attributed to lifetime of the triplet states of the aza-BODIPY. These experimental results indicate that only Br atoms at 2,6 positions enhance the ISC mechanism due to the internal heavy atom effect [7]. Enhanced ISC mechanism also causes fluorescence signal reducing drastically as observed in the fluorescence measurements in Fig.…”

“…There has been a great deal of interest on intersystem crossing (ISC) process of novel materials due to their related applications in photochemical and photophysical processes, such as photodynamic therapy (PDT) [1][2][3][4][5], photocatalytic organic reactions [6][7][8][9][10][11], triplet-triplet annihilation (TTA), upconversion (UC), and singlet oxygen generation [12,13]. ISC process is an efficient way to generate singlet oxygen especially for PDT application.…”

Solar Synthesis: Prospects in Visible Light Photocatalysis

“…Motivated by the important role that nitrogen-containing compounds play in the chemistry of bioactive small molecules, researchers have recently explored the amine radical cations generated by photocatalytic one-electron oxidation of tertiary amines as substrates for synthetic modification (37). One of the most characteristic features of amine radical cations is an observed decrease in the pKa of the C–H bond adjacent to the nitrogen, deprotonation of which results in the formation of nucleophilic α-amino radicals that are capable of reacting with a diverse range of electrophilic reaction partners (38) (Fig.…”

α‐Arylation/Heteroarylation of Chiral α‐Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross‐Coupling Catalysis

“…In the current context, efforts were thus directed toward the generation of α-amino radicals starting from chiral N -trifluoroboratomethyl salts. These versatile α-amino radicals [6,27–35] were envisioned to allow the assembly of enantioenriched building blocks of potential value. [6,28] …”