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Updated: Sep 12, 2025
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Copper Hydride-Catalyzed Net Hydroformylation of Unactivated Terminal Olefins
Subhash Garhwal1, Dennis A Kutateladze1, Binh Khanh Mai2
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
None:
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 (SE2) mechanism with retention of configuration of the reacting Cu-C bond.
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