ABSTRACT
We report novel iridium(III)-catalyzed reactions that afford substituted indoles via the indirect functionalization of alcohols via C-3 selective alkylation of indoles with alcohols and a one-pot cascade strategy from amino- or nitro-phenyl ethyl alcohols, which incorporates oxidative cyclization and C-3 alkylation.
Subject(s)
Alcohols/chemistry , Indoles/chemical synthesis , Alkylation , Catalysis , Cyclization , IridiumABSTRACT
Microwave assisted indirect functionalization of alcohols with 1,3-dimethylbarbituric acid followed by spirocyclisation employing a sequential one-pot Ir(III)/Pd(0) catalysed process, involving the formation of three new C-C bonds, one spirocyclic ring and one di- or tri-substituted exocyclic alkene, is described.
Subject(s)
Alkadienes/chemistry , Barbiturates/chemical synthesis , Iridium/chemistry , Palladium/chemistry , Alkylation , Barbiturates/chemistry , Benzyl Alcohols/chemistry , Catalysis , Crystallography, X-Ray , Cyclization , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/chemistry , Microwaves , Models, Molecular , Molecular Conformation , Molecular Structure , Spiro Compounds/chemical synthesis , Spiro Compounds/chemistry , StereoisomerismABSTRACT
Our objectives were to develop catalytic atom-economic processes accessing and/or incorporating versatile functionality using aryl/heteroaryl acetonitriles as substrates. We report essentially solvent-free [Cp*IrCl2]2 catalyzed redox neutral processes whereby substituted acetonitriles react with primary alcohols to deliver monosubstituted aryl/heteroaryl acetonitriles in excellent yield. We further demonstrate that such processes can be achieved by conventional or microwave heating and that bis- and tris-primary alcohols are also processed efficiently.
Subject(s)
Acetonitriles/chemistryABSTRACT
Palladium catalysed [2 + 2 + 1] cycloaddition of 1,6-heptadiynes with CO (1 atm) furnishes bicyclo[3.3.0]octa-1,5-dien-3-ones in 30-74% yield.
