A wide range of diaryl sulfides and aryl alkyl sulfides are synthesized under mild reaction conditions from the corresponding aryl iodides and aromatic/aliphatic thiols through Ullmann-type intermolecular coupling reactions in the presence of catalytic amount of easily available novel trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol-copper(I) bromide complex at 82 C. The catalytic system is not only capable of coupling electron-withdrawing and electron-releasing substituent-containing substrates, but also tolerates a broad range of functional groups including heteroatom-containing aryl iodides and thiols.

Govindasamy Sekar

Department Of Chemistry

D. J. C. Prasad

Bond formation

COPPER CATALYST

sulfide

THIOETHER

THIOETHERS

anthracene

catalysis

CATALYSTS

Chemical bonds

Copper

Functional groups

Synthesis (chemical)

Copper compounds

anthracene derivative

copper complex

iodide

thiol derivative

article

catalyst

chemical analysis

chemical reaction

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

Synthesis

A direct synthetic route for the C-S coupling of aryl halides with thiophenols is described. This method is tolerant to electron-withdrawing and electron-donating functional groups and also to the presence of functional groups in the ortho position of the aryl iodide or thiophenol. Aryl iodides are coupled with thiophenols without affecting the other functionalities present in the aryl ring. These reactions follow second-order kinetics. Copyright © 2012 John Wiley & Sons, Ltd.

Applied Organometallic Chemistry

Bi(III)-catalyzed C-S cross-coupling reaction

(Chemical Equation Presented) A wide range of diaryl ethers and alkyl aryl ethers are synthesized through intermolecular C(aryl)-O bond formation from the corresponding aryl iodides/aryl bromides and phenols/alcohols through Ullmann-type coupling reaction in the presence of a catalytic amount of easily available (±)-diol L3-CuI complex under very mild reaction conditions. Less reactive aryl bromides can also be used for O-arylation of phenols under the same reaction conditions without increasing the reaction temperature, catalyst loading, and time. The catalytic system not only is capable of coupling hindered substrate but also tolerates a broad range of a series of functional groups. © 2009 American Chemical Society.

Journal of Organic Chemistry

General, mild, and intermolecular Ullmann-type synthesis of diaryl and alkyl aryl ethers catalyzed by diol-copper(I) complex

A wide range of diaryl thioethers and aryl alkyl thioethers are synthesized from the corresponding aryl iodides and aromatic/aliphatic thiols through Ullmann type intermolecular coupling reactions in the presence of a catalytic amount of easily available BINAM-Cu(OTf)2 complex. Less reactive aryl bromides have also been shown to react with thiols under identical reaction conditions to give good yields of the thioethers without increasing the reaction temperature and time. © 2009 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

An efficient intermolecular C(aryl)-S bond forming reaction catalyzed by BINAM-copper(II) complex

Comprehensive Organic Name Reactions and Reagents

Jones Oxidation

Corrigendum to “Enantioselective total synthesis of pyrroloquinolone as a potent PDE5 inhibitor” [Tetrahedron Lett. 50 (2009) 520]

Simple, efficient and recyclable catalytic system for performing copper-catalyzed C–S coupling of thiols with aryl iodides in PEG and PEG–H2O

An efficient, mild and intermolecular ullmann-type synthesis of thioethers catalyzed by a diol-copper(I) complex

Journal	Synthesis
ISSN	00397881
Open Access	No