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Volumn 17, Issue 26, 2011, Pages 7298-7303

Exploring the oxidative cyclization of substituted N-aryl enamines: Pd-catalyzed formation of indoles from anilines

Author keywords

anilines; C C coupling; C H activation; indoles; palladium

Indexed keywords

C-C COUPLING; C-H ACTIVATION; ENAMINES; INDOLES; ONE POT; ONE STEP; OXIDATIVE COUPLINGS; OXIDATIVE CYCLIZATION; SUBSTITUTED INDOLES;

EID: 79958826716     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100631     Document Type: Article
Times cited : (164)

References (84)
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    • For reviews on transition-metal-catalyzed synthesis of indoles, see
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    • For further details see the Supporting Information
    • For further details see the Supporting Information.
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    • For selected examples, see
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    • Very poor conversion was observed when using optimized reaction conditions
    • Very poor conversion was observed when using optimized reaction conditions.
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    • Notably, a small amount of pyrazole product was observed by using MeCN as the solvent, see:, J. J. Neumann, M. Suri, F. Glorius, Angew. Chem. 2010, 122, 7957
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    • As an example of the value of this method, we quote the cost of purchasing the starting materials and the product in 99 % purity from Sigma-Aldrich for one transformation: aniline: 25.70 Euro per L; ethyl acetoacetate: 38 Euro per 1 kg; ethyl-2-methylindole-3-carboxylate: 67.20 Euro per g
    • As an example of the value of this method, we quote the cost of purchasing the starting materials and the product in 99 % purity from Sigma-Aldrich for one transformation: aniline: 25.70 Euro per L; ethyl acetoacetate: 38 Euro per 1 kg; ethyl-2-methylindole-3-carboxylate: 67.20 Euro per g.
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    • An initial olefin-palladium π complex should also be considered, see:, F. Glorius, Angew. Chem. 2004, 116, 3444
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    • Following our initial report on this indole formation, a number of research groups reported powerful related methods: Pd-catalyzed
    • Following our initial report on this indole formation, a number of research groups reported powerful related methods: Pd-catalyzed
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    • by using a hypervalent iodine reagent, not transition-metal-catalyzed
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    • Fe-catalyzed
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.