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Vinyl Nosylates: An Ideal Partner for Palladium‐Catalyzed Cross‐Coupling Reactions
Author(s) -
Cheval Nicolas P.,
Dikova Anna,
Blanc Aurélien,
Weibel JeanMarc,
Pale Patrick
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300127
Subject(s) - palladium , catalysis , ideal (ethics) , coupling reaction , coupling (piping) , materials science , chemistry , organic chemistry , political science , composite material , law
In a hurry to leave! Nosylates act as an excellent leaving group in various palladium‐catalyzed cross‐couplings, such as Suzuki, Stille, Heck, and Sonogashira reactions (see scheme). Crystalline, stable, and cheap vinyl and aryl nosylates proved better than classical halides and triflates, consistently giving higher yields of coupling products. Their usefulness in CC bond formation was also demonstrated by the rapid synthesis of the alkaloid dubamine.