ABSTRACT
An esterification and amination of benzylic C-H bonds was developed by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under metal- and iodide-free conditions. Both carboxylic acids and amines could be used as ideal coupling partners for the oxidative coupling reactions with various diarylmethanes. A close to equal amount of coupling reagents was enough to afford the product in good to high yields.
Subject(s)
Amines/chemistry , Benzhydryl Compounds/chemistry , Benzoquinones/chemistry , Amination , Benzhydryl Compounds/chemical synthesis , Carboxylic Acids/chemistry , Esterification , Models, Chemical , Oxidation-ReductionABSTRACT
A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.
Subject(s)
Copper/chemistry , Sulfinic Acids/chemistry , Sulfinic Acids/chemical synthesis , CatalysisABSTRACT
An iron-catalyzed sulfenylation and arylation of alkynes with aryl sulfinic acid sodium salts is described. Various aromatic sodium sulfinates acted both as aryl and sulfenylation reagents, affording tetrasubstituted alkenes in one pot with good yields.
Subject(s)
Alkenes/chemistry , Alkynes/chemistry , Iron/chemistry , Sodium/chemistry , Sulfinic Acids/chemistry , Catalysis , Crystallography, X-RayABSTRACT
A novel palladium catalyzed approach to 3-arylindoles was developed from indoles and cyclohexanones. Various cyclohexanones acted as aryl sources via an alkylation and dehydrogenation sequence using molecular oxygen as the hydrogen acceptor. This method showed good regioselectivity and afforded 3-arylindoles as the sole products.
Subject(s)
Cyclohexanones/chemistry , Heterocyclic Compounds, 3-Ring/chemical synthesis , Indoles/chemistry , Indoles/chemical synthesis , Palladium/chemistry , Catalysis , Combinatorial Chemistry Techniques , Heterocyclic Compounds, 3-Ring/chemistry , Molecular StructureABSTRACT
A novel approach for the synthesis of 2,3-diarylquinazolinones using iron as catalyst is described. Various 2-nitro-N-arylbenzamides reacted with benzylic alcohols to selectively give the corresponding products in the absence of external oxidant or reductant.
Subject(s)
Alcohols/chemistry , Benzamides/chemistry , Iron/chemistry , Nitro Compounds/chemistry , Quinazolinones/chemical synthesis , Catalysis , Combinatorial Chemistry Techniques , Molecular Structure , Quinazolinones/chemistryABSTRACT
A palladium-catalyzed desulfitative hydroarylation of alkynes with aryl sulfinic acid sodium salts is described. The reaction showed good regio- and stereoselectivity, and afforded the hydroarylation products in good yields. Various functional groups were well tolerated under the optimized reaction conditions.
Subject(s)
Alkynes/chemistry , Organometallic Compounds/chemistry , Palladium/chemistry , Sodium/chemistry , Sulfinic Acids/chemistry , Catalysis , Molecular StructureABSTRACT
The first palladium-catalyzed diarylamine formation from nitroarenes and cyclohexanone derivatives using borrowed hydrogen is described. Various diarylamines were selectively obtained in good to excellent yields. The reaction tolerated a wide range of functionalities. The nitro reduction, cyclohexanone dehydrogenation, and imine formation and reduction were realized in a cascade without an external reducing reagent and oxidant.
ABSTRACT
A palladium-catalyzed desulfitative C-H arylation of azoles with sodium sulfinates using Cu(OAc)(2)·H(2)O as oxidant has been discovered. The reaction proceeded well for a range of different substrates under oxidative conditions. A series of aryl-substituted azoles have been synthesized in moderate to good yields.
