Iron‐Catalyzed Oxidative C−C and N−N Coupling of Diarylamines and Synthesis of Spiroacridines
- 5 December 2016
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 56 (2) , 549-553
Abstract
We describe iron‐catalyzed intermolecular oxidative coupling reactions of diarylamines to form substituted 2,2′‐bis(arylamino)biaryl compounds, tetraarylhydrazines, and 5,6‐dihydrobenzo[c]cinnolines with the same hexadecafluorinated iron–phthalocyanine catalyst. The mild formation of C−C or N−N bonds was controlled by the use of acidic or basic additives. In contrast to most iron‐catalyzed dehydrogenative coupling reactions, ambient air could be used as the sole oxidant. Moreover, iron(III) chloride hexahydrate promoted a one‐pot coupling and subsequent intramolecular dearomative coupling to give 10H‐spiro[acridine‐9,1′‐cyclohexa‐2′,5′‐dien‐4′‐ones].Keywords
This publication has 70 references indexed in Scilit:
- Comparison of Oxidative Aromatic Coupling and the Scholl ReactionAngewandte Chemie International Edition, 2013
- Iron-catalyzed aryl-aryl cross coupling route for the synthesis of 1-(2-amino)-phenyl)dibenzo[b,d]furan-2-ol derivatives and their biological evaluationRSC Advances, 2013
- Catalytic Asymmetric Benzidine RearrangementAngewandte Chemie International Edition, 2013
- Catalytic Asymmetric Benzidine RearrangementAngewandte Chemie, 2013
- Iron-Catalyzed Regioselective Direct Oxidative Aryl–Aryl Cross-CouplingThe Journal of Organic Chemistry, 2011
- Iron(III)-Promoted Oxidative Coupling of Naphthylamines: Synthetic and Mechanistic InvestigationsOrganic Letters, 2011
- PdII‐Catalyzed Aerobic Allylic Oxidative Carbocyclization of Allene‐Substituted Olefins: Immobilization of an Oxygen‐Activating CatalystAngewandte Chemie, 2006
- Fluorinated iron phthalocyanineInorganic Chemistry, 1969
- The Initial Step in the Action of Acids on TetraarylhydrazinesJournal of the American Chemical Society, 1942
- Reversible Photochemical Processes in Rigid Media: The Dissociation of Organic Molecules into Radicals and IonsJournal of the American Chemical Society, 1942