Insertion of Pyridine into the Calcium Allyl Bond: Regioselective 1,4-Dihydropyridine Formation and C----H Bond Activation

The remarkable balance between nucleophilicity and basicity that is found for bis(allyl)calcium has not been previously reported for organolithium and organomagnesium reagents. Pyridine undergoes regioselective 1,4‐insertion into the calcium allyl bond of bis(allyl)calcium. The resulting calcium 4‐a...

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Published inAngewandte Chemie (International ed.) Vol. 49; no. 42; pp. 7795 - 7798
Main Authors Jochmann, Phillip, Dols, Thomas S, Spaniol, Thomas P, Perrin, Lionel, Maron, Laurent, Okuda, Jun
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 11.10.2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
Allyl Compounds - chemistry
allyl ligands
calcium
Calcium - chemistry
Chemistry
Chemistry, Multidisciplinary
CC coupling
CH activation
density functional calculations
Dihydropyridines - chemical synthesis
Dihydropyridines - chemistry
Hydrogen Bonding
Molecular Structure
Organometallic Compounds - chemistry
Physical Sciences
Pyridines - chemistry
Science & Technology
Stereoisomerism
C-C coupling
CATALYSIS
calcium
CONVENIENT METHOD
COMPLEXES
1-ACYLPYRIDINIUM SALTS
allyl ligands
REARRANGEMENT
density functional calculations
C-H activation
CHEMISTRY
METAL
GRIGNARD-REAGENTS
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Summary:The remarkable balance between nucleophilicity and basicity that is found for bis(allyl)calcium has not been previously reported for organolithium and organomagnesium reagents. Pyridine undergoes regioselective 1,4‐insertion into the calcium allyl bond of bis(allyl)calcium. The resulting calcium 4‐allyl‐1,4‐dihydropyridyl compound can be readily converted into the N‐protected 1,4‐dihydropyridine derivatives.
Bibliography:http://dx.doi.org/10.1002/anie.201003704
Financial support by the NRW Forschungsschule "BrenaRo" (scholarship to P.J.) and by the Cluster of Excellence "Tailor Made Fuels from Biomass" is gratefully acknowledged. L.P. and L.M. thank the CINES and CALMIP for a generous grant of computing time. L.M. is member of the Institut Universitaire de France. V. Leich is gratefully acknowledged for his contribution to this work.
ArticleID:ANIE201003704
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Financial support by the NRW Forschungsschule “BrenaRo” (scholarship to P.J.) and by the Cluster of Excellence “Tailor Made Fuels from Biomass” is gratefully acknowledged. L.P. and L.M. thank the CINES and CALMIP for a generous grant of computing time. L.M. is member of the Institut Universitaire de France. V. Leich is gratefully acknowledged for his contribution to this work.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201003704