Metal-free visible-light carbonylation of alkyl iodides to amides via consecutive photoinduced electron transfer
Year: 2026
Type: article
Abstract: A visible-light-driven, metal-free carbonylation of unactivated alkyl iodides is reported, enabling the direct synthesis of 35 structurally diverse amides in good to excellent yields. The reaction shows broad functional-group tolerance toward both amines and alkyl iodides, including bioisosteric motifs and complex natural product derivatives, underscoring its potential for late-stage functionalization. Mechanistic investigations combining flash photolysis, spectroelectrochemistry, irradiated thin-layer cyclic voltammetry, and EPR spectroscopy reveal a consecutive photoinduced electron transfer (ConPET) mechanism that diverges from conventional single-photon photoredox catalysis. DFT calculations elucidate the key radical carbonylation steps governing reactivity and selectivity. This sustainable and operationally simple method offers a transition-metal-free approach to carbonylation, expanding the toolbox for highly reducing transformations under mild conditions.
Source: Chemical Science
DOI: 10.1039/d5sc09778a
Institutions: Centre National de la Recherche Scientifique, Laboratoire Lorrain de Chimie Moléculaire, Université de Lorraine, Laboratoire de Chimie et Physique - Approche Multi-échelle des Milieux Complexes, Institut de Chimie de Strasbourg, Université de Strasbourg, Université de Reims Champagne-Ardenne, Commissariat à l'Énergie Atomique et aux Énergies Alternatives, Université Paris-Saclay, Institut de Biologie Intégrative de la Cellule, CEA Paris-Saclay, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Max Planck Institute for Chemical Energy Conversion
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W7118931180