Incorporating Unbiased, Unactivated Aliphatic Alkenes in Pd(II)-Catalyzed Olefination of Benzyl Phosphonamide

The use of unbiased aliphatic alkene as the coupling partner for C–H olefination continues to be a challenging task. A suitable chelating directing group allowed ortho C–H olefination of benzyl phosphonamide with unactivated aliphatic alkenes. The broad substrate scope with respect to variation of b...

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Published inACS catalysis Vol. 7; no. 11; pp. 7732 - 7736
Main Authors Seth, Kapileswar, Bera, Milan, Brochetta, Massimo, Agasti, Soumitra, Das, Ashis, Gandini, Andrea, Porta, Alessio, Zanoni, Giuseppe, Maiti, Debabrata
Format Journal Article
LanguageEnglish
Published American Chemical Society 03.11.2017
Subjects
unactivated aliphatic alkene
palladium catalyst
sequential hetero-bis-olefination
C−H olefination
gram-scale synthesis
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Abstract The use of unbiased aliphatic alkene as the coupling partner for C–H olefination continues to be a challenging task. A suitable chelating directing group allowed ortho C–H olefination of benzyl phosphonamide with unactivated aliphatic alkenes. The broad substrate scope with respect to variation of benzyl phosphonamides and aliphatic alkenes as well as examples of sequential hetero-bis-olefinations offer diversity along with excellent linear/branch selectivity.
AbstractList The use of unbiased aliphatic alkene as the coupling partner for C–H olefination continues to be a challenging task. A suitable chelating directing group allowed ortho C–H olefination of benzyl phosphonamide with unactivated aliphatic alkenes. The broad substrate scope with respect to variation of benzyl phosphonamides and aliphatic alkenes as well as examples of sequential hetero-bis-olefinations offer diversity along with excellent linear/branch selectivity.
Author Bera, Milan
Brochetta, Massimo
Porta, Alessio
Agasti, Soumitra
Zanoni, Giuseppe
Das, Ashis
Gandini, Andrea
Maiti, Debabrata
Seth, Kapileswar
AuthorAffiliation Department of Chemistry
Dipartimento di Chimica
Università di Pavia
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  email: dmaiti@chem.iitb.ac.in
  organization: Università di Pavia
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Keywords unactivated aliphatic alkene
palladium catalyst
sequential hetero-bis-olefination
C−H olefination
gram-scale synthesis
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Snippet The use of unbiased aliphatic alkene as the coupling partner for C–H olefination continues to be a challenging task. A suitable chelating directing group...
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Title Incorporating Unbiased, Unactivated Aliphatic Alkenes in Pd(II)-Catalyzed Olefination of Benzyl Phosphonamide
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