메뉴 건너뛰기




Volumn 129, Issue 19, 2007, Pages 6149-6167

Mechanistic investigation of intramolecular aminoalkene and aminoalkyne hydroamination/cyclization catalyzed by highly electrophilic, tetravalent constrained geometry 4d and 5f complexes. Evidence for an M-N σ-bonded insertive pathway

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYSTS; CYCLIZATION; NITROGEN COMPOUNDS; PHASE TRANSITIONS; ZIRCONIUM COMPOUNDS;

EID: 34249082758     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0675898     Document Type: Article
Times cited : (189)

References (154)
  • 1
    • 33846347487 scopus 로고    scopus 로고
    • For general hydroamination reviews, see: a
    • For general hydroamination reviews, see: (a) Odom, A. L. Dalton Trans. 2005, 225-233.
    • (2005) Dalton Trans , pp. 225-233
    • Odom, A.L.1
  • 5
    • 4143082679 scopus 로고    scopus 로고
    • (e) Doye, S. Synlett 2004, 1653-1672.
    • (2004) Synlett , pp. 1653-1672
    • Doye, S.1
  • 11
    • 0013272402 scopus 로고    scopus 로고
    • Togni, A, Gruetzmacher, H, Eds, Wiley-VCH: New York
    • (k) Togni, A. In Catalytic Heterofunctionalization; Togni, A., Gruetzmacher, H., Eds.; Wiley-VCH: New York, 2001; pp 91-141.
    • (2001) Catalytic Heterofunctionalization , pp. 91-141
    • Togni, A.1
  • 16
    • 0037031724 scopus 로고    scopus 로고
    • (b) Hartwig, J. F. Science 2002, 297, 1653-1654.
    • (2002) Science , vol.297 , pp. 1653-1654
    • Hartwig, J.F.1
  • 43
    • 34248997987 scopus 로고    scopus 로고
    • For additional examples of group 3 and lanthanide catalyzed intramolecular HA, see: (a) Bambirra, S.; Tsurugi, H.; van Leusen, D.; Hessen, B. Dalton Trans. 2006, 1157-1161.
    • For additional examples of group 3 and lanthanide catalyzed intramolecular HA, see: (a) Bambirra, S.; Tsurugi, H.; van Leusen, D.; Hessen, B. Dalton Trans. 2006, 1157-1161.
  • 63
    • 33644931605 scopus 로고    scopus 로고
    • A slightly modified pathway arguing in favor of turnover-limiting heterocycle protonolysis in intramolecular aminoallene and aminodiene HA/cyclization was proposed from DFT calculations, a Tobisch, S. Chem, Eur. J. 2006, 12, 2520-2531
    • A slightly modified pathway arguing in favor of turnover-limiting heterocycle protonolysis in intramolecular aminoallene and aminodiene HA/cyclization was proposed from DFT calculations. (a) Tobisch, S. Chem. - Eur. J. 2006, 12, 2520-2531.
  • 91
    • 34249039421 scopus 로고    scopus 로고
    • See Supporting Information for full details
    • See Supporting Information for full details.
  • 97
    • 34249034815 scopus 로고    scopus 로고
    • 3 migration to N; see also ref 3p). (Chemical Equation Presented)
    • 3 migration to N; see also ref 3p). (Chemical Equation Presented)
  • 101
    • 34249046543 scopus 로고    scopus 로고
    • 6 solvent mixture to 60°C in the absence of substrate leads to rapid decomposition of 1 and formation of an uncharacterized product.
    • 6 solvent mixture to 60°C in the absence of substrate leads to rapid decomposition of 1 and formation of an uncharacterized product.
  • 108
    • 1542296467 scopus 로고
    • For recent reviews on the chemistry of 4f and 5f elements, see: a, Abel, E. W, Stone, F. G. A, Wilkinson, G, Eds, Pergamon: New York
    • For recent reviews on the chemistry of 4f and 5f elements, see: (a) Burns, C. J.; Neu, M. P.; Boukhalfa, H.; Gutowski, K. E.; Bridges, N. J.; Rogers, R. D. In Comprehensive Coordination Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 4, pp 189-345.
    • (1995) Comprehensive Coordination Chemistry II , vol.4 , pp. 189-345
    • Burns, C.J.1    Neu, M.P.2    Boukhalfa, H.3    Gutowski, K.E.4    Bridges, N.J.5    Rogers, R.D.6
  • 112
    • 0000969532 scopus 로고
    • Abel, E. W, Stone, F. G. A, Wilkinson, G, Eds, Pergamon: New York
    • (e) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 4, pp 11-213.
    • (1995) Comprehensive Organometallic Chemistry II , vol.4 , pp. 11-213
    • Edelmann, F.T.1
  • 123
    • 2142821412 scopus 로고    scopus 로고
    • For reviews of constrained geometry catalysts, see: a
    • For reviews of constrained geometry catalysts, see: (a) Gromada, J.; Carpentier, J.-F.; Mortreux, A. Coord. Chem. Rev. 2004, 248, 397-410.
    • (2004) Coord. Chem. Rev , vol.248 , pp. 397-410
    • Gromada, J.1    Carpentier, J.-F.2    Mortreux, A.3
  • 127
    • 25444458609 scopus 로고    scopus 로고
    • For examples of L2An=NR complexes and their reactivity, see: (a) Zi, G, Blosch, L. L, Jia, L, Andersen, R. A. Organometallics 2005, 24, 4602-4612
    • 2An=NR complexes and their reactivity, see: (a) Zi, G.; Blosch, L. L.; Jia, L.; Andersen, R. A. Organometallics 2005, 24, 4602-4612.
  • 137
    • 34249018735 scopus 로고    scopus 로고
    • For the following pathway, where [A] = [M=NR]: (Equation Presented)
    • For the following pathway, where [A] = [M=NR]: (Equation Presented)
  • 146
    • 28844457653 scopus 로고    scopus 로고
    • An analogous mechanism is invoked in imidotitanium synthesis: Hazari, N, Mountford, P. Acc. Chem. Res. 2005, 38, 839-849
    • An analogous mechanism is invoked in imidotitanium synthesis: Hazari, N.; Mountford, P. Acc. Chem. Res. 2005, 38, 839-849.
  • 152
    • 34249094659 scopus 로고    scopus 로고
    • The experimentally determined ΔS‡, 44.5(8) eu for intermolecular HA is representative of a bimolecular C≡C insertion process, as opposed to the unimolecular insertion proposed for intramolecular HA/cyclization ΔS‡ ca, 30 eu, See ref 1d for details
    • ‡ ca. -30 eu). See ref 1d for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.