Harnessing the Potential of Electron Donor–Acceptor Complexes and N-Centered Radicals: Expanding the Frontiers of Isoquinoline Derivative Synthesis

Abstract

Research on synthesizing nitrogen-containing heterocyclic scaffolds is important because these structures are commonly found in Nature, such as in the alkaloids’ family. In our study, we propose a new method to synthesize the isoquinoline core using an electron donor–acceptor (EDA) complex strategy. Our mechanistic investigations have confirmed that our synthesis process operates through an EDA mechanism, which is not extensively discussed in the literature, particularly regarding its applications on alkynyl substrates. This EDA strategy has proven to be a simple and straightforward way to produce isoquinoline scaffolds and their derivatives without the need for metal catalysts.

N–H Insertion of Anilines on N-Tosylhydrazones Induced by Visible Light Irradiation

“…Given this context and our keen interest in photoinduced C–N bond formation , as well as diazo chemistry, , we were intrigued by investigating photochemical N–H insertion reactions of amines with in situ generated diazo compounds from N -tosylhydrazones. Here, we describe a gentle and metal-free method for Csp 3 -N bond formation through a carbene transfer reaction (Scheme C).…”

N-H Insertion of Anilines on N-Tosylhydrazones Induced by Visible Light Irradiation

“…15 Finally, Koenigs et al have demonstrated a metal-free photochemical carbene-transfer for efficient cyclopropanation, C-H and N-H insertion reaction starting from aryl-N-tosyl hydrazones acetates. 16 Given this context and our keen interest in photoinduced C-N bond formation 18,19 as well as diazo chemistry, 20,21 we were intrigued by investigating photochemical N-H insertion reactions of amines with in-situ generated diazo compounds from N-tosylhydrazones. Here we describe a gentle and metal-free method for Csp 3 -N bond formation through a carbene transfer reaction (Scheme 1C).…”