- Nickel-catalyzed reaction of arylzinc reagents with N-aromatic heterocycles: A straightforward approach to C-H bond arylation of electron-deficient heteroaromatic compounds
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(Chemical Equation Presented) The reaction of electron-deficient N-heteroaromatic compounds, such as pyridines and quinolines, with arylzinc reagents in the presence of a catalytic amount of a nickel complex affords the arylated products. The reaction is likely to proceed through a formal nucleophilic 1,2-addition, thus exhibiting a reactivity complementary to conventional direct arylation through electrophilic substitution.
- Tobisu, Mamoru,Hyodo, Isao,Chatani, Naoto
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- Catalytic arylation of a C-H bond in pyridine and related six-membered N-heteroarenes using organozinc reagents
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Despite significant advances in the catalytic direct arylation of heteroarenes, the application of this reaction to pyridines has been met with limited success. An oxidative nucleophilic arylation strategy has been developed to overcome this problem. Pyridine, pyrazine, quinolone, and related electron-deficient N-heteroarenes can be arylated at the most electrophilic site using the developed nickel-catalyzed reaction. This protocol serves as a complementary method to catalytic direct arylation reactions. Less is more: Pyridine, pyrazine, quinoline and related electron-deficient N-heteroarenes can be arylated at the most electrophilic site using organozinc reagents through nickel catalysis. This protocol serves as a complementary method to catalytic direct arylation reactions. Copyright
- Hyodo, Isao,Tobisu, Mamoru,Chatani, Naoto
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supporting information; experimental part
p. 1357 - 1365
(2012/08/08)
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