Highly Reactive Dicationic Iridium(III) Catalyst for the Polarized Nazarov Cyclization Reaction

Pushing the Nazarov envelope: An electrophilic complex (1; see scheme; EDG=electron‐donating group, EWG=electron‐withdrawing group, binap=2,2‐bis(diphenylphosphanyl)‐1,1‐binaphthyl) exhibits unusual catalytic activity in the polarized Nazarov cyclization reaction. Aryl vinyl ketones that show poor r...

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Published inAngewandte Chemie (International ed.) Vol. 49; no. 19; pp. 3363 - 3366
Main Authors Vaidya, Tulaza, Atesin, Abdurrahman C, Herrick, Ildiko R, Frontier, Alison J, Eisenberg, Richard
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 26.04.2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
Catalysis
Cations - chemistry
Chemistry
Chemistry, Multidisciplinary
Cyclization
homogeneous catalysis
iridium
Iridium - chemistry
Ketones - chemistry
Lewis acids
Physical Sciences
Science & Technology
ACTIVATION
(+/-)-MERRILACTONE-A
COMPLEXES
Lewis acids
COORDINATION SITES
cyclization
iridium
STREPTOMYCES SP
EFFICIENT CATALYSIS
homogeneous catalysis
ROSEOPHILIN
DIIODOBENZENE
STEREOSELECTIVE-SYNTHESIS
CHELATION
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Summary:Pushing the Nazarov envelope: An electrophilic complex (1; see scheme; EDG=electron‐donating group, EWG=electron‐withdrawing group, binap=2,2‐bis(diphenylphosphanyl)‐1,1‐binaphthyl) exhibits unusual catalytic activity in the polarized Nazarov cyclization reaction. Aryl vinyl ketones that show poor reactivity with well‐known catalysts can be readily cyclized with 1/AgSbF6 (1:1) under mild reaction conditions with concurrent AgBr precipitation.
Bibliography:http://dx.doi.org/10.1002/anie.201000100
ArticleID:ANIE201000100
We thank the National Science Foundation (Grants CHE-0556225 and CHE-0847851) for supporting this work. We also thank Dr. Jing Zhang and Dr. Kevin Cariou for helpful discussions, Dr. William Brennessel (University of Rochester) for X-ray crystallography, and Dr. Alice Bergmann (SUNY Buffalo) for high-resolution mass spectrometry.
National Science Foundation - No. CHE-0556225; No. CHE-0847851
ark:/67375/WNG-STJ0QDXF-0
istex:D2F16A04F719FE7F52D2B358F126E1CDEFB52D2A
We thank the National Science Foundation (Grants CHE‐0556225 and CHE‐0847851) for supporting this work. We also thank Dr. Jing Zhang and Dr. Kevin Cariou for helpful discussions, Dr. William Brennessel (University of Rochester) for X‐ray crystallography, and Dr. Alice Bergmann (SUNY Buffalo) for high‐resolution mass spectrometry.
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201000100