The conversion of lignin by catalytic fast pyrolysis into useful fine chemicals is a promising route to fuel production, however selectivity and conversion are still not optimal. Here, the authors investigate the reaction mechanism by detection of reactive intermediates r…

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Understanding the mechanism of catalytic fast pyrolysis by unveiling reactive intermediates in heterogeneous catalysis.

Mild and efficient copper-catalyzed N-arylation of alkylamines and N-H heterocycles using an oxime-phosphine oxide ligand

A Rh(III)-catalyzed highly efficient C6-alkylation of 2-pyridones has been achieved successfully with α-diazo carbonyl compounds. The developed method is simple, mild, and highly regioselective with a broad range of substrate scope. The regioselectivity is guided by the pyridyl substituent attached to the nitrogen center of the pyridone ring. The directing group can be easily removed, and the only formed byproduct is nitrogen. Furthermore, other similar heterocyclic scaffolds can also be functionalized regioselectively under the developed conditions.

C6-Selective Direct Alkylation of Pyridones with Diazo Compounds under Rh(III)-Catalyzed Mild Conditions.

A new method for the synthesis of oxazoles, and in particular chiral non-racemic oxazoles derived from amino acids, has been developed. Thus, rhodium(II) catalysed reaction of diazocarbonyl compounds 6 and 11 in the presence of amides 8 and 10 results in regioselective insertion of the carbenoid into the amide N–H bond with formation of the β-carbonyl amides 9 and 12. Cyclodehydration of amides 9 and 12 using triphenylphosphine–iodine–triethylamine gives functionalised oxazoles 7 and 13. The oxazoles 13c and 13f were converted into the bis-oxazoles 17a and 17b by a second rhodium(II) catalysed regioselective N–H insertion reaction on the amides 15, followed by cyclodehydration.

Synthesis of functionalised oxazoles and bis-oxazoles1

A highly efficient copper-catalyzed system using commercially available racemic 1,1'-binaphthyl-2,2'-diol (rac-BINOL) as the ligand was developed for amination of aryl halides and heteroaryl halides with alkyl amines and N-H heterocycles. Good to high yields were obtained for aryl bromides and heteroaryl chlorides. The commercially available rac-BINOL ligand with excellent stability and high efficiency for aryl bromides and heteroaryl chlorides ultimately make this protocol of potentially practical utility. (c) 2006 Elsevier B.V. All rights reserved.

Efficient copper-catalyzed amination of aryl halides with amines and N-H heterocycles using rac-BINOL as ligand

Facile Synthesis of Alkyl Phenyl Ethers Using Cesium Carbonate

An Improved and Efficient Method for Diazo Transfer Reaction of Active Methylene Compounds

A highly efficient alkylation method of phenols using alkyl halide/cesium carbonate/acetonitrile system is described.

Facile Synthesis of Alkyl Phenyl Ethers Using Cesium Carbonate.

Diazo transfer reactions between active methylene compounds and the p-toluenesulfonyl azide can be efficiently mediated in the presence of cesium carbonate.

Jong Yeob Yuk

Papers

Facile Synthesis of Alkyl Phenyl Ethers Using Cesium Carbonate

An Improved and Efficient Method for Diazo Transfer Reaction of Active Methylene Compounds

Facile Synthesis of Alkyl Phenyl Ethers Using Cesium Carbonate.

An Improved and Efficient Method for Diazo Transfer Reaction of Active Methylene Compounds.