Synthesis of Aryl-methylene Ethers through Pd(0)-Catalyzed Coupling between Hydrobenzoxazoles and Dichloromethane

Using dichloromethane (DCM) as the C1 feedstock, the first Pd(0)-catalyzed synthesis of aryl-methylene ether motifs from hydrobenzoxazoles (hydrothiazoles) has been reported. This protocol has exhibited an ample substrate scope (38 examples) and wide functional group tolerance. Aryl-methylene ether adducts have been successfully engaged in coupling with isocyanate to provide bis-iminoisoindolinones. In this reaction, DCM has served as a twofold electrophile for reaction with hydrobenzoxazoles via double C-Cl bond cleavage.

Automated summary

The first Pd(0)-catalyzed synthesis of aryl-methylene ethers from hydrobenzoxazoles (hydrothiazoles) using dichloromethane (DCM) as the C1 feedstock is reported. This protocol demonstrates a broad substrate scope (38 examples) and wide tolerance to functional groups. The aryl-methylene ether adducts have been successfully coupled with isocyanate to provide bis-iminoisoindolinones. In this reaction, DCM serves as a twofold electrophile, undergoing double C-Cl bond cleavage to react with hydrobenzoxazoles.