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Merck
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  • Iron-catalyzed oxidative direct α-C-H bond functionalization of cyclic ethers: selective C-O bond formation in the presence of a labile aldehyde group.

Iron-catalyzed oxidative direct α-C-H bond functionalization of cyclic ethers: selective C-O bond formation in the presence of a labile aldehyde group.

Organic letters (2014-03-19)
Balaji D Barve, Yang-Chang Wu, Mohamed El-Shazly, Michal Korinek, Yuan-Bin Cheng, Jeh-Jeng Wang, Fang-Rong Chang
ABSTRACT

Iron catalyzed oxidative coupling of salicylaldehydes with cyclic ethers proceeded through the direct α-C-H functionalization of ethers, forming the corresponding acetals in moderate to excellent yields. This is the first example of iron catalyzed selective C-O bond formation in the presence of a sensitive aldehyde moiety.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Salicylaldehyde, reagent grade, 98%
Sigma-Aldrich
Salicylaldehyde, redist., ≥99.0% (GC)
Supelco
Salicylaldehyde, analytical standard
Sigma-Aldrich
Salicylaldehyde, ≥98%, FG