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Volumn 51, Issue 79, 2015, Pages 14781-14784

3-Aza π-allyl palladium derived from imino migration in palladium-carbene: MCRs toward multiple substituted indole skeleton

Author keywords

[No Author keywords available]

Indexed keywords

2 IODOANILINE; ANILINE; CARBENE; HYDRAZONE DERIVATIVE; INDOLE; ISONITRILE DERIVATIVE; N TOSYLHYDRAZONE DERIVATIVE; PALLADIUM; PHOSPHINE; UNCLASSIFIED DRUG;

EID: 84942155068     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c5cc05984d     Document Type: Article
Times cited : (18)

References (39)
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  • 29
    • 84896539422 scopus 로고    scopus 로고
    • For selected reviews on isocyanide in organic synthesis, see
    • L. Zhang Acc. Chem. Res. 2014 47 877
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    • Zhang, L.1
  • 32
    • 84878651302 scopus 로고    scopus 로고
    • For the palladium-catalyzed amidation of N-tosylhydrazone with isonitrile, see
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    • (2013) Chem. Soc. Rev. , vol.42 , pp. 5257
    • Qiu, G.1    Ding, Q.2    Wu, J.3
  • 37
    • 0025111749 scopus 로고
    • One of the reviewers suggested an alternative pathway leading to 5. Transimination between the aniline and aryl hydrazone starting materials provides an iminium intermediate. Then, oxidative addition ArI to Pd(0) and insertion into the isocyanide took place. After that, the intramolecular migratory insertion into the iminium followed by β-hydride elimination regenerates the Pd(0) catalyst and forms iminium intermediate F. According to his helpful suggestion, we tested the reaction under the same conditions using N-(2-iodophenyl)-1-phenylmethanimine and phenylisocyanide. However, no compounds 5 was detected, which ruled out the possibility of this pathway
    • M. J. O'Donnell X. Yang M. Li Tetrahedron Lett. 1990 31 5135
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5135
    • O'Donnell, M.J.1    Yang, X.2    Li, M.3
  • 39


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.