Versatile Carbon−Carbon Bond-Forming Polycondensation between Terpene Derivatives and Malonic Esters via Palladium-Catalyzed Allylic Substitution Reaction

2003 ◽  
Vol 36 (9) ◽  
pp. 3007-3009 ◽  
Author(s):  
Nobuyoshi Nomura ◽  
Nao Yoshida ◽  
Ko Tsurugi ◽  
Keigo Aoi
Keyword(s):  
Substitution Reaction ◽  
Allylic Substitution ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed ◽  
Terpene Derivatives

scholarly journals Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

2016 ◽  
Vol 12 ◽  
pp. 2898-2905 ◽  
Author(s):  
Michal Medvecký ◽  
Igor Linder ◽  
Luise Schefzig ◽  
Hans-Ulrich Reissig ◽  
Reinhold Zimmer
Keyword(s):  
Click Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
High Efficacy ◽  
Carbon Bond ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed ◽  
Oxazine Derivatives

Iodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor.

scholarly journals Palladium-Catalyzed Carbon?Carbon Bond-Forming 1,2-Ligand Migration of Organoalanes.

ChemInform ◽  
2005 ◽  
Vol 36 (15) ◽  
Author(s):  
Eric Fillion ◽  
Rebekah J. Carson ◽  
Vincent E. Trepanier ◽  
Julie M. Goll ◽  
Anna A. Remorova
Keyword(s):  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Ligand Migration ◽  
Palladium Catalyzed
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