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1.
Org Biomol Chem ; 12(24): 4252-9, 2014 Jun 28.
Article in English | MEDLINE | ID: mdl-24838670

ABSTRACT

Direct metal-free C-4-selective indolation of pyridines is achieved for the first time using TEMPO and (Boc)2O. A variety of substituents on both indoles and pyridines are tolerated to give 3-(pyridin-4-yl)-1H-indole derivatives in moderate to excellent yields. This finding provides a novel approach for developing metal-free C-H functionalization of pyridines.


Subject(s)
Carbonates/chemistry , Cyclic N-Oxides/chemistry , Indoles/chemistry , Metals/chemistry , Pyridines/chemistry , Alkylation , Oxidation-Reduction , Stereoisomerism
2.
Org Biomol Chem ; 11(45): 7938-45, 2013 Dec 07.
Article in English | MEDLINE | ID: mdl-24135895

ABSTRACT

A general and efficient method for the cross-coupling of indoles with ß-keto esters by using TEMPO/CuSO4·5H2O in air as oxidant has been developed. This reaction features high functional-group compatibility and an excellent selectivity. This methodology provides an alternative approach for the ketonization-olefination of indoles in moderate to good yields.


Subject(s)
Alkenes/chemical synthesis , Copper/chemistry , Indoles/chemistry , Ketones/chemical synthesis , Alkenes/chemistry , Catalysis , Cyclic N-Oxides/chemistry , Esters/chemistry , Ketones/chemistry , Molecular Structure , Stereoisomerism
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