Photoredox-catalyzed regioselective allene alkoxycarbonylations for the synthesis of α-allyl-γ-lactones
Year: 2025
Type: article
Abstract: A dual photoredox/hydrogen atom transfer (HAT) strategy for the radical alkoxycarbonylation of allenes is described. Alkoxycarbonyl radicals, generated by photoredox-catalyzed decarboxylation of alkyl oxalic acids, add to the proximal carbon of allene precursors with high regioselectivity to furnish α-allyl-γ-lactone products in up to 92% yield. The intermediate vinyl radicals can be trapped by a hydrogen atom or by a heteroatom using selenium and iodine transfer reagents. The alkene and vinyl moieties are readily post-functionalized to furnish more complex molecular scaffolds, highlighting the synthetic utility offered using the combination of allenes and oxalic acids as compared to their alkene and oxalate salt counterparts.
Source: Chemical Science
DOI: 10.1039/d5sc02854j
Authors: Elijah T. Marris, Ashley L. Palecek, Federico Barbieri, Derek B. Hu, Ken S. Lee, Jennifer M. Schomaker
Institutions: University of Wisconsin–Madison, University of Pavia
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W4411613809