Synthesis 2022; 54(20): 4551-4560
DOI: 10.1055/a-1884-6988
paper

One-Pot Synthesis of Diaryl Sulfonamides using an Iron- and Copper-Catalyzed Aryl C–H Amidation Process

Lachlan J. N. Waddell
a   School of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK
,
Martyn C. Henry
a   School of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK
,
Mohamed A. B. Mostafa
a   School of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK
,
a   School of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK
› Institutsangaben

We are grateful for funding from the Engineering and Physical Sciences­ Research Council (EPSRC) (Ph.D. studentships to L.J.N.W., EP/T517896/1 and M.C.H., EP/M508056/1). Financial support from the Ministry of Higher Education and Scientific Research, the University of Benghazi, Libya (studentship to M.A.B.M.) and the University of Glasgow is gratefully acknowledged.


Abstract

A one-pot, two-stage synthesis of diaryl sulfonamides using sequential iron and copper catalysis is developed. Regioselective para-iodination of activated arenes by the super Lewis acid, iron triflimide and N-iodosuccinimide (NIS), is followed by a copper(I)-catalyzed N-arylation reaction. The process is found to be applicable for the coupling of a range of anisoles, anilines and acetanilides with primary sulfonamides and is used for the one-pot synthesis of biologically important compounds.

Supporting Information



Publikationsverlauf

Eingereicht: 01. Juni 2022

Angenommen nach Revision: 24. Juni 2022

Accepted Manuscript online:
24. Juni 2022

Artikel online veröffentlicht:
27. Juli 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany