Catalytic Hydroamination of Alkynes and Norbornene with Neutral and Cationic Tantalum Imido Complexes

Several tantalum imido complexes have been synthesized and shown to efficiently catalyze the hydroamination of internal and terminal alkynes. An unusual hydroamination/hydroarylation reaction of norbornene catalyzed by a highly electrophilic cationic tantalum imido complex is also reported. Factors...

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Bibliographic Details
Published inOrganic letters Vol. 6; no. 15; pp. 2519 - 2522
Main Authors Anderson, Laura L, Arnold, John, Bergman, Robert G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.07.2004
Amer Chemical Soc
Subjects
Alkynes - chemistry
Amination
Catalysis
Chemistry
Chemistry, Organic
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Structure
Norbornanes - chemistry
Organometallic Compounds - chemical synthesis
Physical Sciences
Science & Technology
Tantalum - chemistry
ALKENES
ZIRCONIUM
MECHANISM
INTERMOLECULAR HYDROAMINATION
TITANIUM PRECATALYST
ANILINE
INTRAMOLECULAR HYDROAMINATION
REACTIVITY
COORDINATION
REDUCTIVE ELIMINATION
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Summary:Several tantalum imido complexes have been synthesized and shown to efficiently catalyze the hydroamination of internal and terminal alkynes. An unusual hydroamination/hydroarylation reaction of norbornene catalyzed by a highly electrophilic cationic tantalum imido complex is also reported. Factors affecting catalyst activity and selectivity are discussed along with mechanistic insights gained from stoichiometric reactions.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0492851