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Volumn 75, Issue 11, 2010, Pages 3900-3903

Palladium-catalyzed intramolecular amidation of C(sp2)-H bonds: Synthesis of 4-aryl-2-quinolinones

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHLORINE COMPOUNDS; COPPER COMPOUNDS; PALLADIUM;

EID: 77952971084     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100557s     Document Type: Article
Times cited : (106)

References (86)
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    • Pd-catalyzed functionalizations of 2-quinolinones were also reported; see, for example
    • Pd-catalyzed functionalizations of 2-quinolinones were also reported; see, for example: Wang, A.; Wang, B.; Wu, J. J. Comb. Chem. 2007, 9, 811-817
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    • Examples of C-S bond formation via catalytic C-H functionalization are much rarer in the literature; see: Zhao, X.; Dimitrijević, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 3466-3467
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    • note
    • Heating independently prepared 1-tosyl-4-phenyl-2-quinolinone at 120 °C in DMSO in the absence of palladium and copper salts resulted in the detosylation, producing compound 2 in quantitative yield. Similar detosylation has been previously reported; see ref 8e.
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    • For detailed results of screening, see the Supporting Information
    • For detailed results of screening, see the Supporting Information.
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    • 2), because of its nontoxic, readily available, and easy-to-handle character, can be considered as one of the most ideal reoxidants and has often been employed as a terminal co-reoxidant for similar catalytic C-H functionalization processes; see ref 12c,12f,12g,12k. For other selected recent examples, see
    • 2), because of its nontoxic, readily available, and easy-to-handle character, can be considered as one of the most ideal reoxidants and has often been employed as a terminal co-reoxidant for similar catalytic C-H functionalization processes; see ref 12c,12f,12g,12k. For other selected recent examples, see: Ueda, S.; Nagasawa, H. J. Org. Chem. 2009, 74, 4272-4277
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    • note
    • E -/ Z -Isomerization of 1s was observed when either 1s-Z or 1s-E was heated in DMSO at 120 °C for 8 h, resulting in the formation of a 1:1.9 mixture of E -/ Z -isomers from both isomers.
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    • D) of 3.5 (intramolecular) and 2.7 (intermolecular), indicating that cleavage of the C-H bond is involved in the rate-determining step. Similar KIE values (intramolecular: 3.5, intremolecular: 2.6) were previously observed in a related aromatic palladation process; see:;, For experimental details, see the Supporting Information
    • D) of 3.5 (intramolecular) and 2.7 (intermolecular), indicating that cleavage of the C-H bond is involved in the rate-determining step. Similar KIE values (intramolecular: 3.5, intremolecular: 2.6) were previously observed in a related aromatic palladation process; see: Chernyak, N.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 5636-5637 For experimental details, see the Supporting Information.
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    • note
    • 2 atmosphere for the reactions of 1k - v gives better results in terms of the yield and the reaction time.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.