Palladium‐Catalyzed Cross‐Coupling of Furfuryl Alcohols with Arylboronic Acids via Aromatization‐Driven Carbon−Carbon Bond Cleavage to Synthesize 5‐Arylfurfuryl Alcohols and 2,5‐Diaryl Furans

2019 ◽  
Vol 361 (24) ◽  
pp. 5576-5586 ◽  
Author(s):  
Guanghao Huang ◽  
Biaolin Yin
Keyword(s):  
Bond Cleavage ◽  
Cross Coupling ◽  
Carbon Bond ◽  
Arylboronic Acids ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed

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.

ChemInform Abstract: Palladium-Catalyzed Arylative Carbon-Carbon Bond Cleavage of α,α-Disubstituted Arylmethanols.

ChemInform ◽  
2010 ◽  
Vol 33 (6) ◽  
pp. no-no
Author(s):  
Yoshito Terao ◽  
Hiroyuki Wakui ◽  
Tetsuya Satoh ◽  
Masahiro Miura ◽  
Masakatsu Nomura
Keyword(s):  
Bond Cleavage ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed

Carbon-Carbon Bond Formation: Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones with Allylic Alcohols

2012 ◽  
Vol 18 (34) ◽  
pp. 10497-10500 ◽  
Author(s):  
Huoji Chen ◽  
Li Huang ◽  
Wei Fu ◽  
Xiaohang Liu ◽  
Huanfeng Jiang
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Allylic Alcohols ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed
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