A wide range of N-arylated indoles are selectively synthesized through intermolecular C(aryl)-N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of a catalytic amount of easily available N,N,N′,N′-tetramethyl-BINAM-CuI complex under very mild reaction conditions. © 2009 Elsevier Ltd. All rights reserved.

Govindasamy Sekar

Department Of Chemistry

R. Koteshwar Rao

copper derivative

indole derivative

iodide

polycyclic aromatic hydrocarbon derivative

article

arylation

catalysis

chemical bond

chemical reaction

priority journal

productivity

stereochemistry

synthesis

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Tetrahedron

A wide range of 2-aryl or 2-alkyl-substituted benzothiazoles are synthesized through intramolecular C(aryl)-S bond forming-cyclization using copper(II)-BINAM-catalyzed coupling of less reactive N-(2-chlorophenyl) benzo or alkylthioamide under mild reaction conditions (82 °C). © 2010 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides

Direct oxidation of primary alcohols to the corresponding carboxylic acids is performed highly efficiently at room temperature with anhydrous tert-butyl hydroperoxide in the presence of a catalytic amount of easily available CuCl under ligand free conditions in acetonitrile. Benzylic alcohols are more reactive than aliphatic alcohols, and these benzylic alcohols are selectively oxidized to the corresponding acids in the presence of aliphatic alcohols such as 1-octanol and 1-decanol. © 2008 Elsevier Ltd. All rights reserved.

CuCl catalyzed selective oxidation of primary alcohols to carboxylic acids with tert-butyl hydroperoxide at room temperature

A wide range of diaryl ethers are synthesized from the corresponding aryl iodides and phenols through Ullmann type coupling reactions in the presence of a catalytic amount of easily available BINAM-Cu(OTf)2 complex under mild reaction conditions. Less reactive aryl bromides have also been shown to react with phenols under identical reaction conditions to give good yields of the diaryl ethers without increasing the reaction temperature and time. © 2007 Elsevier Ltd. All rights reserved.

An efficient BINAM-copper(II) catalyzed Ullmann-type synthesis of diaryl ethers

A DABCO-copper(I) chloride complex (5 mol%) together with TEMPO (5 mol%) in nitromethane as solvent has been used as an efficient catalytic system for the selective oxidation of benzylic and allylic alcohols into the corresponding carbonyl compounds at room temperature where molecular oxygen acts as an ultimate, stoichiometric oxidant and water is the only by-product. The solidstate structure determination of the DABCOcopper complex shows that the copper is in the + II oxidation state with trigonal bipyramidal geometry and exists in a linear polymeric structure due to strong hydrogen bonding. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

Advanced Synthesis and Catalysis

Aerobic, chemoselective oxidation of alcohols to carbonyl compounds catalyzed by a DABCO-copper complex under mild conditions

Sax's Dangerous Properties of Industrial Materials

1-(4-Methoxy-2-Methyl-5-Phenyl-1H-Pyrrol-3-Yl)Ethanone 91480-98-7

ChemSpider Synthetic Pages

Olefination of 6-bromo-1H-indole-2,3-dione with 1H-indol-3-yl acetate via the 2-chloroindoleninone

An efficient, mild, and selective Ullmann-type N-arylation of indoles catalyzed by copper(I) complex

Journal	Tetrahedron
ISSN	00404020
Open Access	No