15796-70-0Relevant articles and documents
Efforts directed toward the synthesis of colchicine: Application of palladium-catalyzed siloxane cross-coupling methodology
Seganish, W. Michael,Handy, Christopher J.,DeShong, Philip
, p. 8948 - 8955 (2007/10/03)
Colchicine is an important and synthetically challenging natural product. The key synthetic step in this approach to the synthesis of colchicine involved a palladium-catalyzed cross-coupling reaction between 5-bromotropolone (4) and an aryl siloxane to form the aryl-tropolone bond. The coupling of a variety of highly functionalized aryl siloxane derivatives was investigated and optimized coupling conditions were developed. It was discovered that a palladium catalyst with a high degree of phosphine ligand coordination (5 equiv of phosphine/mol Pd) was necessary to efficiently couple aryl siloxanes with 5-bromotropolone (4). In addition, the coupling approach has provided a direct comparison between siloxane and boronic acid coupling technologies that demonstrated that aryl siloxanes and boronic acids produce similar yields of highly functionalized biaryl products.
Syntheses and ipso-substitution reactions of some C-stannylated troponoids
Banwell, Martin G.,Cameron, Jennifer M.,Collis, Maree P.,Gravatt, G. Lance
, p. 395 - 407 (2007/10/03)
The C-stannylated troponoids (2)-(8) have been prepared and two of these shown to undergo palladium(0)-catalysed cross-coupling with bromobenzene to give the corresponding phenyl-substituted tropone. Compounds (3), (5) and (6)-(8) all react with electrophiles to give products of ipso-substitution.
A CONVENIENT SYNTHESIS OF 5-ARYLTROPONES
Keenan, Richard M.,Kruse, Lawrence I.
, p. 793 - 798 (2007/10/02)
2-methoxy-5-oxy>tropone was coupled to a variety of arylzinc chlorides in the presence of a palladium catalyst to furnish 5-aryltropones in good to excelent yields.
