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Volumn 7, Issue 13, 2005, Pages 2519-2522

Directed ortho metalation methodology. The N,N-dialkyl aryl O-sulfamate as a new directed metalation group and cross-coupling partner for grignard reagents

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Indexed keywords


EID: 27144479191     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050393c     Document Type: Article
Times cited : (142)

References (55)
  • 2
  • 17
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    • and references cited therein
    • Iron-catalyzed coupling: Fürstner, A.; Martin, R. Angew. Chem., Int. Ed. 2004, 43, 3955 and references cited therein.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3955
    • Fürstner, A.1    Martin, R.2
  • 21
    • 2342449966 scopus 로고    scopus 로고
    • and refs cited therein
    • A useful element of the O-carbamate is its proclivity for anionic ortho Fries rearrangement exposing a phenol that, upon triflation and Ni-catalyzed hydride reduction, also achieves its removal with retention of a new amide DMG for further DoM chemistry; see: Cai, X.; Brown, S.; Hodson, P.; Snieckus, V. Can. J. Chem. 2004, 82, 195 and refs cited therein.
    • (2004) Can. J. Chem. , vol.82 , pp. 195
    • Cai, X.1    Brown, S.2    Hodson, P.3    Snieckus, V.4
  • 27
    • 0345791433 scopus 로고    scopus 로고
    • and refs cited therein
    • For use of O-sulfamates in Ru-catalyzed C-H-activated processes, see: Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823 and refs cited therein.
    • (2003) Org. Lett. , vol.5 , pp. 4823
    • Wehn, P.M.1    Lee, J.2    Du Bois, J.3
  • 33
    • 1642320259 scopus 로고    scopus 로고
    • Suzuki-Miyaura
    • DoM chemistry of this function has, to the best of our knowledge, not been achieved. For cross-coupling chemistry, see: Tang, Z.-Y.; Hu, Q.-S. J. Am. Chem. Soc. 2004, 126, 3058 (Suzuki-Miyaura).
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 3058
    • Tang, Z.-Y.1    Hu, Q.-S.2
  • 37
    • 84952507887 scopus 로고
    • Benzyne generation may be achieved by elimination from 1,2-dihalides; see: Wittig, G.; Benz, E. Chem. Ber. 1959, 92, 1999.
    • (1959) Chem. Ber. , vol.92 , pp. 1999
    • Wittig, G.1    Benz, E.2
  • 47
    • 33845550671 scopus 로고
    • In an attempt to trap the thermodynamically generated anion, treatment of 3 under Martin conditions (1g: LiTMP/TMSCl = 1:2.1:10) (Krizan, T. D.; Martin, J. C. J. Am. Chem. Soc. 1983, 105, 6155) led to SM (35%), 4e (41%), and 2,2,6,6-tetramethyl-1-(2-(trimethylsilyl)phenyl)-piperidine (19%) by GC analysis.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6155
    • Krizan, T.D.1    Martin, J.C.2
  • 49
    • 29844453785 scopus 로고    scopus 로고
    • note
    • Generalization of this result is being pursued.
  • 52
    • 0035903607 scopus 로고    scopus 로고
    • High activity of NiClCpIMes may be attributed to the presence of a low-valent electron-rich metal center owing to a strongly Lewis basic, electron σ-donating carbene ligand whose steric nature accelerates the reductive elimination step, see: Bohm, V. P. W.; Gstottmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3387
    • Bohm, V.P.W.1    Gstottmayr, C.W.K.2    Weskamp, T.3    Herrmann, W.A.4
  • 54
    • 29844456644 scopus 로고    scopus 로고
    • note
    • 6 led only to the formation of p-isopropylanisole in low yield.
  • 55
    • 29844435430 scopus 로고    scopus 로고
    • note
    • 4 in PhMe at 90°C for 24 h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.