Copper Hydride-Catalyzed Net Hydroformylation of Unactivated Terminal Olefins
Year: 2025
Type: article
Abstract: We report a copper-catalyzed method for the highly regioselective formal hydroformylation via hydroacetalization of simple terminal alkenes. The robust protocol employs a commercially available diethoxy methyl ester proelectrophile activated by cocatalytic Zn(OTf) 2 and was found to operate on a variety of functionalized olefin substrates to provide acetal products with exclusive linear regioselectivity. Density functional theory studies support that the key C–C bond forming event between the alkyl copper and the oxocarbenium ion intermediates takes place via a frontside electrophilic substitution (S E 2) mechanism with retention of configuration of the reacting Cu–C bond.
Source: Organic Letters
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: G1309160875, G5124643077, Category I. Computing without Boundaries: Cyberinfrastructure for the Long Tail of Science, MRI: Acquisition of Cutting-Edge GPU and MPI Nodes for the Interdisciplinary Pitt Center for Research Computing, Category I: Bridges-2: Scalable Converged Computing, Data, and Analytics for Rapidly Evolving Science and Engineering Research, Metal-Catalyzed Methods for Organic Synthesis, Peptide-Conjugated Palladium Oxidative Addition Complexes for Site-Selective Arylation Chemistry
OpenAlex ID: W4412659714