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For a recent example employing organozincs as a nucleophilic arylating reagent for the catalytic direct arylation of azines, see
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For a non-regioselective direct arylation of azines with aryl iodides promoted by KO t -Bu, see
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For the use of acid chlorides and acid anhydrides as electrophilic arylating reagents in Rh(I)-catalyzed direct arylation of arenes, see
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For the use of acid chlorides and acid anhydrides as electrophilic arylating reagents in Rh(I)-catalyzed direct arylation of arenes, see: Zhao, X.; Yu, Z. J. Am. Chem. Soc. 2008, 130, 8136
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84904445733
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For a complete list of optimization parameters examined, refer to ref 9
-
For a complete list of optimization parameters examined, refer to ref 9.
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-
-
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31
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84904445734
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The use of benzoic acid anhydride was also evaluated; in this case, only trace cross-coupling product was detected
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The use of benzoic acid anhydride was also evaluated; in this case, only trace cross-coupling product was detected.
-
-
-
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32
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84904445735
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2, 37%
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2, 37%.
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33
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84904445736
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Similar results were obtained with other substituted pyridines and diazenes; under identical conditions, the coupling of 2-(3-pentyl)pyridine with 3,5-dimethylbenzoyl chloride afforded a 16% yield of 2-(3,5-dimethylphenyl)-6- (3-pentyl)pyridine, while the coupling of 2,3-dimethylpyrazine with 3,5-dimethylbenzoyl chloride afforded a 31% assay yield of 2-(3,5- dimethylphenyl)-5,6-dimethylpyrazine
-
Similar results were obtained with other substituted pyridines and diazenes; under identical conditions, the coupling of 2-(3-pentyl)pyridine with 3,5-dimethylbenzoyl chloride afforded a 16% yield of 2-(3,5-dimethylphenyl)-6- (3-pentyl)pyridine, while the coupling of 2,3-dimethylpyrazine with 3,5-dimethylbenzoyl chloride afforded a 31% assay yield of 2-(3,5- dimethylphenyl)-5,6-dimethylpyrazine.
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84904445737
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For the related Rh-catalyzed alkylation of azines with alkenes, C-H activation is followed by alkene insertion, suggesting the competence of C-H activation prior to ArBr or aroyl chloride activation. See ref 8a
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For the related Rh-catalyzed alkylation of azines with alkenes, C-H activation is followed by alkene insertion, suggesting the competence of C-H activation prior to ArBr or aroyl chloride activation. See ref 8a.
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