Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts

Sandro Cacchi; Giancarlo Fabrizi; Antonella Goggiamani; Luca M Parisi; Roberta Bernini

doi:10.1021/jo0493469

Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts

J Org Chem. 2004 Aug 20;69(17):5608-14. doi: 10.1021/jo0493469.

Authors

Sandro Cacchi¹, Giancarlo Fabrizi, Antonella Goggiamani, Luca M Parisi, Roberta Bernini

Affiliation

¹ Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi "La Sapienza", P. le A. Moro 5, 00185 Rome, Italy. [email protected]

PMID: 15307729
DOI: 10.1021/jo0493469

Abstract

The palladium-catalyzed reaction of sulfinic acid salts with a wide variety of aryl and vinyl halides or triflates provides unsymmetrical diaryl sulfones and aryl vinyl sulfones in good to excellent yields. The reaction is strongly influenced by the presence of nBu4NCl, and the use of Xantphos, a rigid bidentate ligand with a wide natural bite angle, was found to be crucial for the success of the reaction. With neutral, electron-rich, and electron-poor aryl iodides best results were obtained by using Pd2(dba)3, Xantphos, Cs2CO3, and nBu4NCl, in toluene at 80 degrees C. Two general procedures were employed with aryl bromides and triflates: sodium p-toluenesulfinate, Pd2(dba)3, Xantphos, Cs2CO3, 120 degrees C, in toluene with nBu4NCl (procedure A: neutral, electron-rich, and slightly electron-poor aryl bromides or triflates) and without nBu4NCl (procedure B: electron-poor aryl bromides or triflates). With vinyl triflates best results were obtained at 60 degrees C omitting nBu4NCl.