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Published on: May 21, 2019
CO2-DBU-Triggered Photoredox-Catalyzed Direct α-C-H Alkylation of Alcohols
Zeyu Zhang1, Zongchang Han2, Yuhao Shang1
1Department of Chemistry, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing, 100084, P. R. China.
None:
An efficient photoinduced and metal-free method for direct α-C-H monoalkylation of alcohols utilizing the CO2-DBU-system as a hydrogen bond acceptor (HBA) catalyst in the presence of water (H2O) is reported. This protocol allows for selective functionalization of alcohols with a broad substrate scope, demonstrating yields up to 88% in 36 examples. Systematic computational analysis using DFT calculations reveals insights into the mechanism by identifying the key intermediates assembled via intermolecular hydrogen bond between DBU-CO2 adduct and alcohol. This strategy opens new avenues for efficient alkylation of ordinary alcohols, offering an environmentally friendly approach to complex molecular synthesis.
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