PdII-Catalyzed CH Olefination of N-(2-Pyridyl)sulfonyl Anilines and Arylalkylamines

Flexible friend: The N‐(2‐pyridyl)sulfonyl group acts as a removable directing group in the PdII‐catalyzed aryl CH ortho alkenylation of N‐alkyl aniline, benzylamine, and phenethylamine derivatives with electron‐poor alkenes. The products were obtained in high yields (70–90 %) and with complete reg...

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Published inAngewandte Chemie (International ed.) Vol. 50; no. 46; pp. 10927 - 10931
Main Authors García-Rubia, Alfonso, Urones, Beatriz, Gómez Arrayás, Ramón, Carretero, Juan C.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 11.11.2011
WILEY‐VCH Verlag
Wiley
Subjects
2-pyridyl sulfonamides
aniline
Chemistry
Chemistry, Multidisciplinary
CH activation
olefination
palladium
Physical Sciences
Science & Technology
ROOM-TEMPERATURE
DIRECT ALKENYLATION
2-pyridyl sulfonamides
ACTIVATION
ACID
REACTIVITY
DIRECTING GROUPS
FUNCTIONALIZATION
C-H activation
palladium
aniline
DERIVATIVES
olefination
BOND-FORMATION
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Summary:Flexible friend: The N‐(2‐pyridyl)sulfonyl group acts as a removable directing group in the PdII‐catalyzed aryl CH ortho alkenylation of N‐alkyl aniline, benzylamine, and phenethylamine derivatives with electron‐poor alkenes. The products were obtained in high yields (70–90 %) and with complete regiocontrol. The mild reductive N‐sulfonyl removal enables the construction of a variety of nitrogen heterocycles. EWG=electron‐withdrawing group.
Bibliography:This work was supported by the Ministerio de Ciencia e Innovación (MICINN; projects CTQ2006-01121 and CTQ2009-07791) and the Consejería de Educación de la Comunidad de Madrid (programme AVANCAT; S2009/PPQ-1634). A.G.-R. and B.U. thank the MICINN for a predoctoral fellowship. We also thank Johnson Matthey PLC for a generous supply of Pd(OAc)2.
Ministerio de Ciencia e Innovación - No. CTQ2006-01121; No. CTQ2009-07791
ark:/67375/WNG-4W7RK35F-P
ArticleID:ANIE201105611
Consejería de Educación de la Comunidad de Madrid - No. S2009/PPQ-1634
istex:4D699FACF0DC37C62A2D3DEEB0010488ADAB058C
2
.
This work was supported by the Ministerio de Ciencia e Innovación (MICINN; projects CTQ2006‐01121 and CTQ2009‐07791) and the Consejería de Educación de la Comunidad de Madrid (programme AVANCAT; S2009/PPQ‐1634). A.G.‐R. and B.U. thank the MICINN for a predoctoral fellowship. We also thank Johnson Matthey PLC for a generous supply of Pd(OAc)
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201105611