1242653-19-5Relevant academic research and scientific papers
Synthesis of ortho/ortho ′-substituted 1,1-diarylethylenes through cross-coupling reactions of sterically encumbered hydrazones and aryl halides
Roche, Maxime,Hamze, Abdallah,Provot, Olivier,Brion, Jean-Daniel,Alami, Mouad
, p. 445 - 454 (2013/03/13)
The reactivity of sterically hindered N-tosylhydrazones 2 featuring ortho/ortho′-substituents on the aromatic ring with various ortho-, meta-, and para-substituted aryl halides 3 was investigated. To accomplish successfully this challenging coupling, fine-tuning of the reaction conditions were required. The newly established PdCl2(MeCN)2/Xphos/ NaO-t-Bu/F-benzene system in a sealed tube is compatible with a broad spectrum of both coupling partners, regardless of their electronic and steric nature. This protocol has been applied successfully to the synthesis of a xanthene derivative.
Pd-catalyzed reaction of sterically hindered hydrazones with aryl halides: Synthesis of tetra-substituted olefins related to iso-combretastatin A4
Brachet, Etienne,Hamze, Abdallah,Peyrat, Jean-Francois,Brion, Jean-Daniel,Alami, Mouad
supporting information; experimental part, p. 4042 - 4045 (2010/11/16)
PdCl2(MeCN)2 in combination with dppp proved to be a powerful and efficient catalyst for the coupling of sterically hindered N-arylsulfonylhydrazones with aryl halides, thus providing a flexible and convergent access to tetrasubstituted olefins related to iso-combretastatin A4 in good yields. This new protocol has been applied successfully to the formal synthesis of biphenylisopropylidene 4-pyridine CYP17 inhibitor, 12b, of biological interest.
