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Volumn 130, Issue 11, 2008, Pages 3304-3306

Palladium-catalyzed oxidative ethoxycarbonylation of aromatic C-H bond with diethyl azodicarboxylate

Author keywords

[No Author keywords available]

Indexed keywords

AZODICARBOXYLIC ACID DIETHYL ESTER; CARBON; CARBOXYLIC ACID DERIVATIVE; HYDROGEN; PALLADIUM; UNCLASSIFIED DRUG;

EID: 41449116165     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710555g     Document Type: Article
Times cited : (199)

References (56)
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    • Some recent reviews on C-H functionalizations, see a
    • Some recent reviews on C-H functionalizations, see (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
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    • Selected examples for transition metal catalyzed direct carbonylation reactions: for [Ru] (a) Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433 and references therein.
    • Selected examples for transition metal catalyzed direct carbonylation reactions: for [Ru] (a) Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433 and references therein.
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    • For [Pd
    • (b) For [Pd]
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    • For [Rh] (e) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
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    • Mo], and [Cr] (f) Mori, Y.; Tsuji, J
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    • 12] (5 mol%) and DEAD in toluene did not produce 2a in detectable yield with the starting material being recovered (87%).
    • 12] (5 mol%) and DEAD in toluene did not produce 2a in detectable yield with the starting material being recovered (87%).
  • 39
    • 34548217139 scopus 로고    scopus 로고
    • 2 to dibenzyl azodicarboxylate: Muniz, K.; Iglesias, A. Angew. Chem., Int. Ed. 2007, 46, 6350.
    • 2 to dibenzyl azodicarboxylate: Muniz, K.; Iglesias, A. Angew. Chem., Int. Ed. 2007, 46, 6350.
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    • See Supporting Information for details
    • See Supporting Information for details.
  • 41
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    • 2-Et (X-ray structure characterized) was isolated asa side-product in 52% yield from the Pd-catalyzed reaction of 1a with DEAD.
    • 2-Et (X-ray structure characterized) was isolated asa side-product in 52% yield from the Pd-catalyzed reaction of 1a with DEAD.
  • 42
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    • Similar regioselectivity was also reported by Sanford and co-workers for Pd-catalyzed acetoxylation of arylpyridines: Kalyani, D.; Sanford, M. Org. Lett. 2005, 7, 4149. See also refs 5, 6a, and 6c
    • Similar regioselectivity was also reported by Sanford and co-workers for Pd-catalyzed acetoxylation of arylpyridines: Kalyani, D.; Sanford, M. Org. Lett. 2005, 7, 4149. See also refs 5, 6a, and 6c
  • 43
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    • This result may suggest that the higher reactivity of DEAD relative to other azodicarboxylates could have led to the higher product yields observed see Supporting Information
    • This result may suggest that the higher reactivity of DEAD relative to other azodicarboxylates could have led to the higher product yields observed (see Supporting Information).
  • 44
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    • 13C NMR analysis of the unknown revealed a characteristic carbonyl signal at 155.8 ppm, which is unique from dibenzyl carbonate and dibenzyl oxalate. A similar product profile was observed for thermal decomposition of dibenzyl azodicarboxylate.
    • 13C NMR analysis of the unknown revealed a characteristic carbonyl signal at 155.8 ppm, which is unique from dibenzyl carbonate and dibenzyl oxalate. A similar product profile was observed for thermal decomposition of dibenzyl azodicarboxylate.
  • 51
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    • Recent reports on metal catalyzed alkane carbonylation by a free-radical mechanism: (a) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350.
    • Recent reports on metal catalyzed alkane carbonylation by a free-radical mechanism: (a) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350.
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    • IV chemistry, see (a) Canty, A. J. Acc. Chem. Res. 1992, 25, 83.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.