ABSTRACT
A range of secondary and tertiary phenylacetamides undergo oxidative homodimerization to afford biaryls. The reaction proceeds under palladium catalysis in the presence of a copper cocatalyst and oxygen and is most effective for electron-rich substrates.
Subject(s)
Acetanilides/chemistry , Carbon/chemistry , Dimerization , Hydrogen/chemistry , Molecular Structure , Oxidation-ReductionABSTRACT
A new approach to the Fischer-indole synthesis is reported that uses the reactive intermediate benzyne. The addition of N-tosyl hydrazones to arynes, generated through fluoride activation of 2-(trimethylsilyl)phenyl triflate precursors, leads to efficient N-arylation. Addition of a Lewis acid to the same reaction pot then affords N-tosylindole products via Fischer cyclization.
Subject(s)
Benzene Derivatives/chemistry , Indoles/chemical synthesis , Tosyl Compounds/chemical synthesis , Catalysis , Combinatorial Chemistry Techniques , Cyclization , Hydrazones/chemistry , Indoles/chemistry , Molecular Structure , Tosyl Compounds/chemistryABSTRACT
An oxidative C-H coupling is described for medium-ring synthesis.
ABSTRACT
Insertion of benzene rings into the amide bond using the reactive intermediate benzyne is described. Aromatic amides undergo smooth insertion when treated with O-triflatophenyl silane benzyne precursors, producing versatile aminobenzophenone products in good to excellent yield. The process is entirely metal-free and has been exemplified on the synthesis of biologically active acridones and acridines.
