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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Bibliographic Details
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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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.7b02394