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Volumn 129, Issue 37, 2007, Pages 11431-11437

Brønsted acid catalyzed formal insertion of isocyanides into a C-O bond of acetals

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL RESINS; CARBONYLATION; CATALYSIS; CHEMICAL BONDS; FUNCTIONAL GROUPS;

EID: 35048887160     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073286h     Document Type: Article
Times cited : (76)

References (83)
  • 4
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    • The term insertion is intended to describe the formal reaction pattern of the overall transformation and not to imply any mechanistic claim
    • The term "insertion" is intended to describe the formal reaction pattern of the overall transformation and not to imply any mechanistic claim.
  • 33
    • 0347278498 scopus 로고    scopus 로고
    • Reviews on the use of gallium salts in organic synthesis: a
    • Reviews on the use of gallium salts in organic synthesis: (a) Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. Chemtracts 2000, 13, 431.
    • (2000) Chemtracts , vol.13 , pp. 431
    • Yamaguchi, M.1    Tsukagoshi, T.2    Arisawa, M.3
  • 35
    • 0038307508 scopus 로고    scopus 로고
    • For recent examples of gallium(III)-catalyzed reactions by other groups, see: (a) Surya, P. G. K.; Yan, P.; Török, B.; Bucsi, I.; Tanaka, M.; Olah, G. A. Catal. Lett. 2003, 85, 1.
    • For recent examples of gallium(III)-catalyzed reactions by other groups, see: (a) Surya, P. G. K.; Yan, P.; Török, B.; Bucsi, I.; Tanaka, M.; Olah, G. A. Catal. Lett. 2003, 85, 1.
  • 53
    • 35048850581 scopus 로고    scopus 로고
    • Other less active catalysts that were examined: ZrCl4, HfCl4, ReCl(CO)5, FeCl3, PtCl2, AuCl3, Mgl2, Zn(OTf)2, Yb(OTf)3, Hf(OTf)4, Sn(OTf)2, and B(C6F5) 3
    • 3.
  • 62
    • 33745354541 scopus 로고    scopus 로고
    • For the Passerini-type reactions of acetals that lead to α-alkoxy amide, see: Barrett, A. G. M.; Barton, D. H. R.; Falck, J. R.; Papaioannou, D.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 1979, 652. See also ref 28a.
    • For the Passerini-type reactions of acetals that lead to α-alkoxy amide, see: Barrett, A. G. M.; Barton, D. H. R.; Falck, J. R.; Papaioannou, D.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 1979, 652. See also ref 28a.
  • 64
    • 34250848349 scopus 로고    scopus 로고
    • The relative nucleophilicity of isocyanides has been estimated based on the rate constant of the reaction with benzhydrylium ions, although the data for isocyanides 2c and 2d are not available. Tumanov, V. V, Tishkov, A. A, Mayr, H. Angew. Chem, Int. Ed. 2007, 46, 3563
    • The relative nucleophilicity of isocyanides has been estimated based on the rate constant of the reaction with benzhydrylium ions, although the data for isocyanides 2c and 2d are not available. Tumanov, V. V.; Tishkov, A. A.; Mayr, H. Angew. Chem., Int. Ed. 2007, 46, 3563.
  • 65
    • 35048888657 scopus 로고    scopus 로고
    • Benzyl alcohol did not give benzylmethylbenzenes under the reaction conditions, excluding the pathway H → 10.
    • Benzyl alcohol did not give benzylmethylbenzenes under the reaction conditions, excluding the pathway H → 10.
  • 67
    • 35048883596 scopus 로고    scopus 로고
    • Beller, M, Ed, Springer: Heidelberg, Germany
    • Catalytic Carbonylation Reactions; Beller, M., Ed.; Springer: Heidelberg, Germany, 2006.
    • (2006) Catalytic Carbonylation Reactions
  • 68
    • 33746865952 scopus 로고    scopus 로고
    • α-Alkoxy carboxylic acid derivatives exhibit biological activities. For recent examples, see: McDonnell, P. A.; Constantine, K. L.; Goldfarb, V.; Johnson, S. R.; Sulsky, R.; Magnin, D. R.; Robl, J. A.; Caulfield, T. J.; Parker, R. A.; Taylor, D. S.; Adam, L. P.; Metzler, W. J.; Mueller, L.; Farmer, B. T., II. J. Med. Chem. 2006, 49, 5013.
    • α-Alkoxy carboxylic acid derivatives exhibit biological activities. For recent examples, see: McDonnell, P. A.; Constantine, K. L.; Goldfarb, V.; Johnson, S. R.; Sulsky, R.; Magnin, D. R.; Robl, J. A.; Caulfield, T. J.; Parker, R. A.; Taylor, D. S.; Adam, L. P.; Metzler, W. J.; Mueller, L.; Farmer, B. T., II. J. Med. Chem. 2006, 49, 5013.
  • 74
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    • For a recent example of the one-carbon homologation of aldehydes using isocyanides, see
    • For a recent example of the one-carbon homologation of aldehydes using isocyanides, see: Bonne, D.; Dekhane, M.; Zhu, J. J. Am. Chem. Soc. 2005, 127, 6926.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 6926
    • Bonne, D.1    Dekhane, M.2    Zhu, J.3
  • 75
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    • For recent examples of Brønsted acid catalyzed reactions, see
    • For recent examples of Brønsted acid catalyzed reactions, see: Connon, S. J. Angew. Chem., Int. Ed. 2006, 45, 3909.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 3909
    • Connon, S.J.1
  • 81
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    • For recent reviews of multicomponent transformations using isocyanides, see
    • For recent reviews of multicomponent transformations using isocyanides, see: Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
    • (2000) Chem. Eur. J , vol.6 , pp. 3321
    • Bienaymé, H.1    Hulme, C.2    Oddon, G.3    Schmitt, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.