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.

Debashis Chakraborty

Aryl halides

ARYL IODIDES

ARYL RINGS

Cross coupling reactions

Electron-donating

Electronwithdrawing

ORTHO POSITION

SECOND ORDER KINETICS

Synthetic routes

Thiophenols

Water

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

Applied Organometallic Chemistry

An efficient Cu-catalyzed one-pot approach for the synthesis of unsymmetrical diaryl thioethers using potassium ethyl xanthogenate as a thiol surrogate is developed. This new protocol avoids usage of intricate thiols and makes use of its easily available xanthate as a precursor, and thiol will be generated in situ to prepare the diaryl thioethers through a Cu-catalyzed double arylation. This strategy was further successfully utilized for the synthesis of symmetrical diaryl thioethers, aryl alkyl thioethers, and benzothiazoles. (Figure Presented) © 2011 American Chemical Society.

Organic Letters

Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor

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.

Synthesis

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

A variety of aromatic, aliphatic and conjugated aldehydes were converted to the corresponding carboxylic acid derivatives with 30% H2O 2 as the oxidant in the presence of catalytic amounts of AgNO 3. The method described has wide range of applicabilities, does not involve cumbersome work-up, exhibits chemoselectivity and proceeds under mild reaction conditions, and the resulting products are obtained in good yields within reasonable time. © 2009 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

Silver nitrate-catalyzed oxidation of aldehydes to carboxylic acids by H2O2

European Journal of Organic Chemistry

A Highly Efficient Method for the Copper-Catalyzed Selective Synthesis of Diaryl Chalcogenides from Easily Available Chalcogen Sources

The Journal of Organic Chemistry

Copper-Mediated C–H Activation/C–S Cross-Coupling of Heterocycles with Thiols

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

Journal	Applied Organometallic Chemistry
ISSN	02682605
Open Access	No