Coupling of thiols and aromatic halides promoted by diboron derived super electron donors. Issue 88 (20th October 2021)

• Record Type: Journal Article
• Authors: Franco, Mario; Vargas, Emily L.; Tortosa, Mariola; Cid, M. Belén
• Is Part Of: Chemical communications. Volume 57:Issue 88(2021)
• Page Start: 11653
• Page End: 11656
• Publication Date: 2021-10-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc05294b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Diboron-based super electron donors (SEDs) efficiently catalyze the coupling between thiols and aryl halides through a SRN 1 mechanism. Remarkably, under the optimized conditions, the competitive borylation reaction of the aryl halides is suppressed. Abstract : We have proven that pyridine–boryl complexes can be used as superelectron donors to promote the coupling of thiols and aromatic halides through a SRN 1 mechanism. The reaction is efficient for a broad substrate scope, tolerating heterocycles including pyridines, enolizable or reducible functional groups. The method has been applied to intermediates in drug synthesis as well as interesting functionalized polythioethers through a controlled and consecutive intramolecular electron transfer process.