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Volumn 9, Issue 17, 2007, Pages 3351-3353

Lewis acid-promoted imine synthesis by the insertion of isocyanides into C-H bonds of electron-rich aromatic compounds

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EID: 34548152325     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071314v     Document Type: Article
Times cited : (38)

References (35)
  • 1
    • 23744454427 scopus 로고    scopus 로고
    • Murahashi, S.-I. Ed, Thieme, Stuttgart
    • Suginome, M.; Ito, Y. In Science of Synthesis; Murahashi, S.-I. Ed.; Thieme, Stuttgart, 2004, Vol. 19; pp. 445-530.
    • (2004) Science of Synthesis , vol.19 , pp. 445-530
    • Suginome, M.1    Ito, Y.2
  • 8
    • 0000402423 scopus 로고    scopus 로고
    • Reversible addition of weak nucleophiles to isocyanides has been proposed in the intramolecular cyclization of 2-alkynylisocyanobenzenes: Suginome, M, Fukuda, T, Ito, Y. Org. Lett. 1999, 1, 1977
    • Reversible addition of weak nucleophiles to isocyanides has been proposed in the intramolecular cyclization of 2-alkynylisocyanobenzenes: Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
  • 9
    • 0000863229 scopus 로고    scopus 로고
    • B: Jacobsen, H.; Berke, H.; Doring, S.; Kehr, G.; Erker, G.; Frohlich, R.; Mayer, O. Organometallics 1999, 18, 1724.
    • B: Jacobsen, H.; Berke, H.; Doring, S.; Kehr, G.; Erker, G.; Frohlich, R.; Mayer, O. Organometallics 1999, 18, 1724.
  • 10
    • 0000263012 scopus 로고    scopus 로고
    • Al: Fisher, J. D.; Wei, M.-Y.; Willett, R.; Shapiro, P. J. Organometallics 1994, 13, 3324.
    • Al: Fisher, J. D.; Wei, M.-Y.; Willett, R.; Shapiro, P. J. Organometallics 1994, 13, 3324.
  • 11
    • 0040417141 scopus 로고    scopus 로고
    • Zr: Brackemeyer, T.; Erker, G.; Frohlich, R. Organometallics 1997, 16, 531.
    • Zr: Brackemeyer, T.; Erker, G.; Frohlich, R. Organometallics 1997, 16, 531.
  • 12
    • 0000773754 scopus 로고    scopus 로고
    • Ti: Carofiglio, T.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. Inorg. Chem.1989, 28, 4417.
    • Ti: Carofiglio, T.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. Inorg. Chem.1989, 28, 4417.
  • 13
    • 0038541773 scopus 로고    scopus 로고
    • For recent examples of Lewis acid-promoted reactions of isocyanides, see;
    • For recent examples of Lewis acid-promoted reactions of isocyanides, see; Chatani, N.; Oshita, M.; Tobisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 7812
    • Chatani, N.1    Oshita, M.2    Tobisu, M.3    Ishii, Y.4    Murai, S.5
  • 20
    • 34548159220 scopus 로고    scopus 로고
    • The process is closely related to Vilsmeir-Haack reaction, in which chloroiminium salts work as an electrophile. Jones, G.; Stanforth, S. P. Org. React. 1997, 49, 1.
    • The process is closely related to Vilsmeir-Haack reaction, in which chloroiminium salts work as an electrophile. Jones, G.; Stanforth, S. P. Org. React. 1997, 49, 1.
  • 21
    • 34548145569 scopus 로고    scopus 로고
    • 3), but with reduced yields. For example, the isolated yield of entry 12 in Table 1 was 65%.
    • 3), but with reduced yields. For example, the isolated yield of entry 12 in Table 1 was 65%.
  • 22
    • 34548188740 scopus 로고    scopus 로고
    • 4 (24%), HCl (26%), TfOH (51%), and TFA (0%).
    • 4 (24%), HCl (26%), TfOH (51%), and TFA (0%).
  • 28
    • 0001588270 scopus 로고    scopus 로고
    • Transition metal-mediated insertion of isocyanides into the N-H bond in indoles: Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640.
    • Transition metal-mediated insertion of isocyanides into the N-H bond in indoles: Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640.
  • 29
    • 34548149709 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 30
    • 34548192218 scopus 로고    scopus 로고
    • A crossover experiment indicates that the major part of the proton migration occurs intramolecularly, although an intermolecular process can be operating as a minor path. See Supporting Information for details
    • A crossover experiment indicates that the major part of the proton migration occurs intramolecularly, although an intermolecular process can be operating as a minor path. See Supporting Information for details.
  • 31
    • 34548187463 scopus 로고    scopus 로고
    • An alternative mechanistic possibility would be the intermediacy of a 3-indolylmetal species, such as D (see below).18 We observed the interaction between indole 1 and GaCl3 by 1H NMR. However, no such interaction was observed when a 1:1 mixture of 1 and 2a was treated with GaCl3, and only the resonance of 2a was shifted. Thus, we currently believe that the dominant species in our reaction is the isocyanide-Lewis acid adduct, as in A, and the insertion proceeds through A
    • 3, and only the resonance of 2a was shifted. Thus, we currently believe that the dominant species in our reaction is the isocyanide-Lewis acid adduct, as in A, and the insertion proceeds through A.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.