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Volumn 75, Issue 22, 2010, Pages 7863-7868

Rh(I)-catalyzed direct arylation of azines

Author keywords

[No Author keywords available]

Indexed keywords

AIR-STABLE; ARYL BROMIDES; ARYLATIONS; DECARBONYLATIONS; ELECTRON-DEFICIENT; ELECTRON-RICH AROMATICS; GOOD YIELD; REACTION CONDITIONS; TRIFLUOROMETHYL;

EID: 78449241259     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101793r     Document Type: Article
Times cited : (88)

References (41)
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    • For a recent example employing organozincs as a nucleophilic arylating reagent for the catalytic direct arylation of azines, see
    • For a recent example employing organozincs as a nucleophilic arylating reagent for the catalytic direct arylation of azines, see: Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070
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    • For a non-regioselective direct arylation of azines with aryl iodides promoted by KO t -Bu, see
    • For a non-regioselective direct arylation of azines with aryl iodides promoted by KO t -Bu, see: Yanagisawa, S.; Ueda, K.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 4673
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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 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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    • The use of benzoic acid anhydride was also evaluated; in this case, only trace cross-coupling product was detected
    • The use of benzoic acid anhydride was also evaluated; in this case, only trace cross-coupling product was detected.
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    • 2, 37%
    • 2, 37%.
  • 33
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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.
  • 39
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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
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.