Cyclopropylamine‐Derived Distonic Iminium Radicals: Photoinduced Strategies in Chemo‐ and Stereo‐Selective Synthesis
- 1Department of Chemical and Geological Sciences Università degli Studi di Cagliari Complesso Universitario di Monserrato Monserrato Cagliari Italy
Abstract
Cyclopropylamines have emerged as privileged substrates in photocatalysis owing to their propensity to undergo single‑electron oxidation followed by strain‑release β‐scission, generating highly reactive distonic iminium radicals. These intermediates underpin a broad repertoire of light‐driven transformations, including ring‑opening functionalization, formal [3 + 2] cycloadditions, radical cascade processes, and asymmetric bond‐forming reactions. This Review highlights recent advances in the photochemical activation of cyclopropylamines, emphasizing mechanistic insights, catalyst design, and the synthetic potential of these reactions for accessing complex carbocycles, heterocycles, and medicinally relevant scaffolds. This review is organized to first summarize the preparation of cyclopropylamine derivatives, then to discuss their photoinduced rearrangements and ring‑opening pathways, followed by an overview of [3 + 2] cycloadditions, enantioselective strategies, and applications for constructing unconventional building blocks. Together, these developments underscore the growing impact of cyclopropylamine‐derived radicals as versatile tools in modern synthetic methodology.
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BibTeX
@article{cabua2026cyclopropylaminederived,
title = {{Cyclopropylamine‐Derived Distonic Iminium Radicals: Photoinduced Strategies in Chemo‐ and Stereo‐Selective Synthesis}},
author = {Maria Chiara Cabua and Alberto Luridiana and Francesco Secci and Emanuele Cocco},
journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
year = {2026},
month = jul,
doi = {10.1002/chem.71383},
url = {https://doi.org/10.1002/chem.71383},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Cyclopropylamine‐Derived Distonic Iminium Radicals: Photoinduced Strategies in Chemo‐ and Stereo‐Selective Synthesis
AU - Maria Chiara Cabua
AU - Alberto Luridiana
AU - Francesco Secci
AU - Emanuele Cocco
PY - 2026
DA - 2026/07/12
JO - Chemistry (Weinheim an Der Bergstrasse, Germany)
DO - 10.1002/chem.71383
UR - https://doi.org/10.1002/chem.71383
AB - Cyclopropylamines have emerged as privileged substrates in photocatalysis owing to their propensity to undergo single‑electron oxidation followed by strain‑release β‐scission, generating highly reactive distonic iminium radicals. These intermediates underpin a broad repertoire of light‐driven transformations, including ring‑opening functionalization, formal [3 + 2] cycloadditions, radical cascade processes, and asymmetric bond‐forming reactions. This Review highlights recent advances in the photochemical activation of cyclopropylamines, emphasizing mechanistic insights, catalyst design, and the synthetic potential of these reactions for accessing complex carbocycles, heterocycles, and medicinally relevant scaffolds. This review is organized to first summarize the preparation of cyclopropylamine derivatives, then to discuss their photoinduced rearrangements and ring‑opening pathways, followed by an overview of [3 + 2] cycloadditions, enantioselective strategies, and applications for constructing unconventional building blocks. Together, these developments underscore the growing impact of cyclopropylamine‐derived radicals as versatile tools in modern synthetic methodology.
SN - 0947-6539
SN - 1521-3765
ER -