[Cu]-Catalyzed S(N)AR reactions: direct amination of electron deficient aryl halides with sodium azide and the synthesis of arylthioethers under Cu(II)-ascorbate redox system

Title [Cu]-Catalyzed S(N)AR reactions: direct amination of electron deficient aryl halides with sodium azide and the synthesis of arylthioethers under Cu(II)-ascorbate redox system
Publication TypeJournal Article
Year of Publication2010
AuthorsGoriya, Y, Ramana, CV
JournalTetrahedron
Volume66
Issue38
Pagination7642-7650
Date PublishedSEP
ISSN0040-4020
KeywordsAnilines, Azide reduction, Cu(II)-ascorbate redox system, SNAr reaction, Thioether
Abstract

A one pot [Cu]-promoted SNAr reaction of electron-deficient halobenzenes with sodium azide and the reduction of the intermediate aryl azides under the same Cu(II) ascorbate redox conditions leading to anilines has been documented. Control experiments revealed that both ascorbate and proline play important role in the reaction path way. Further, the use of this catalytic Cu(II) ascorbate redox system has been explored for the synthesis of arylthioethers. (C) 2010 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2010.07.032
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.011

Divison category: 
Organic Chemistry