Simple and Sustainable Iron-Catalyzed Aerobic C–H Functionalization of N,N‑Dialkylanilines

Iron(III) chloride catalyzes the aerobic oxidation of tertiary anilines, including tetrahydroisoquinolines, to form reactive iminium ion intermediates that undergo Mannich reactions with silyloxyfurans, nitroalkanes, and other nucleophiles to give the corresponding butenolides, nitro compounds, and...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 135; no. 25; pp. 9475 - 9479
Main Authors Ratnikov, Maxim O, Xu, Xinfang, Doyle, Michael P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.06.2013
Amer Chemical Soc
Subjects
Aniline Compounds - chemical synthesis
Aniline Compounds - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Chlorides - chemistry
Ferric Compounds - chemistry
Molecular Structure
Physical Sciences
Science & Technology
DIOXYGEN
DEHYDROGENATIVE COUPLING REACTIONS
OXIDATIVE MANNICH REACTION
ACID
TERTIARY-AMINES
TRANSITION-METAL
ION
BOND ACTIVATION
N-DEMETHYLATION
MOLECULAR-OXYGEN
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Summary:Iron(III) chloride catalyzes the aerobic oxidation of tertiary anilines, including tetrahydroisoquinolines, to form reactive iminium ion intermediates that undergo Mannich reactions with silyloxyfurans, nitroalkanes, and other nucleophiles to give the corresponding butenolides, nitro compounds, and α-substituted tetrahydroisoquinolines, respectively, in good to excellent yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja402479r