Cu(II)-Catalyzed Functionalizations of Aryl C−H Bonds Using O2 as an Oxidant

Xiao Chen; Xueshi Hao; Charles E. Goodhue; Jin‐Quan Yu

doi:10.1021/ja061715q

Abstract

Cu(II)-catalyzed acetoxylation and halogenation of aryl C−H bonds are developed. ortho-Selectivity was observed with a wide range of 2-arylpyridine substrates. Both mono- and difunctionalizations are achieved by tuning the reaction conditions. Excellent functional group tolerance and use of O2 as a stoichiometric oxidant are significant advantages over our recently developed Pd-catalyzed C−H functionalization reactions. These newly discovered reaction conditions are also applicable for cyanation, amination, etherification, and thioetherification of aryl C−H bonds. Mechanistic investigations are carried out to gain insights into the Cu(II)-catalyzed C−H functionalization reactions.

Keywords

ChemistryCyanationAminationHalogenationCatalysisSurface modificationArylSelectivityCombinatorial chemistryStoichiometryMedicinal chemistryFunctional groupOrganic chemistry

Affiliated Institutions

Brandeis University US

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Publication Info

Year: 2006
Type: article
Volume: 128
Issue: 21
Pages: 6790-6791
Citations: 1369
Access: Closed

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APA Style

                            
                                
                                    Xiao Chen, 
                                
                                    Xueshi Hao, 
                                
                                    Charles E. Goodhue
                                
                                et al.
                            
                            (2006). 
                            Cu(II)-Catalyzed Functionalizations of Aryl C−H Bonds Using O<sub>2</sub> as an Oxidant. 
                            Journal of the American Chemical Society
                            , 128
                            (21)
                            , 6790-6791.
                            https://doi.org/10.1021/ja061715q
                        

Identifiers

DOI: 10.1021/ja061715q

Cu(II)-Catalyzed Functionalizations of Aryl C−H Bonds Using O<sub>2</sub> as an Oxidant