Convenient Synthetic Route to Palladium Complexes of Unconventional N-Heterocyclic Carbenes Derived from Pyridazine and Phthalazine

2012 ◽  
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Tongxun Guo ◽  
Sebastian Dechert ◽  
Steffen Meyer ◽  
Franc Meyer



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Enrica Bortolamiol ◽  
Flavio Rizzolio ◽  
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Fabiano Visentin


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Eric Assen B. Kantchev ◽  
Christopher J. O'Brien ◽  
Michael G. Organ




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...  


2016 ◽  
Vol 71 (6) ◽  
pp. 643-650 ◽  
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Sascha Wiechmann ◽  
Tyll Freese ◽  
Zong Guan ◽  
Andreas Schmidt

AbstractThe anion of N-phenylsydnone, which can be generated on treatment of N-phenylsydnone with cyanomethyllithium without decomposition, can be represented as tripolar zwitterionic and as anionic N-heterocyclic carbene resonance forms. Its palladium complex was prepared from 4-bromo-3-phenylsydnone and tetrakis(triphenylphosphine)palladium and proved to be active as catalyst in Suzuki-Miyaura reactions. Thus, 2,5-dibromo-3,4-dinitrothiophene was effectively converted into 2,5-diaryl-3,4-dinitrothiophenes with 1-naphthyl, (4-trifluoromethoxy)phenyl, [4-(methylsulfanyl)phenyl], and biphenyl-4-yl boronic acid. 3-(Phenanthren-9-yl)quinoline was prepared by Suzuki-Miyaura reaction starting from 3-bromoquinoline. 1-Chloro-2,4-dinitrobenzene cross-coupled with phenyl boronic acid, 1-naphthyl boronic acid, 9-phenanthryl boronic acid. 4-Bromobenzylic alcohol gave (4-isopropylphenyl)methanol on sydnone-palladium complex-catalyzed reaction with isopropyl boronic acid.





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