Metal-free regioselective formation of C-N and C-O bonds with the utilization of diaryliodonium salts in water: facile synthesis of N-arylquinolones and aryloxyquinolines

Regioselective construction of crucial C-N and C-O bonds leading to N-arylquinolones and aryloxyquinolines has been accomplished by employing easily accessible diaryliodonium salts and quinolones in water under metal-and ligand-free conditions. This operationally simple strategy is significant due t...

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Published inOrganic & biomolecular chemistry Vol. 15; no. 23; pp. 4956 - 4961
Main Authors Mehra, Manish Kumar, Tantak, Mukund P., Arun, V., Kumar, Indresh, Kumar, Dalip
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.06.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
H FUNCTIONALIZATION
ROOM-TEMPERATURE
ALIPHATIC-ALCOHOLS
HYPERVALENT IODINE
ONE-POT SYNTHESIS
COUPLING REACTIONS
THIOUREA DIOXIDE
EFFICIENT SYNTHESIS
RECYCLABLE CATALYST
ARYL ETHERS
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Summary:Regioselective construction of crucial C-N and C-O bonds leading to N-arylquinolones and aryloxyquinolines has been accomplished by employing easily accessible diaryliodonium salts and quinolones in water under metal-and ligand-free conditions. This operationally simple strategy is significant due to mild reaction conditions, high product yields, recyclability of released iodoarenes and scalability to the gram level. The practical utility of the developed protocol was proved by the arylation of medicinally important heterocycles like acridin-9(10H)-one, 3-methyl-quinoxalin-2(1H)-one and 1H-benzo[d]imidazol-2(3H)-one.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00940b