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Volumn 28, Issue 12, 2009, Pages 3552-3566

A Theoretical Investigation of the Ni(II)-Catalyzed Hydrovinylation of Styrene

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; CATALYST PRECURSORS; CATALYTIC CYCLES; CATALYTIC SYSTEM; COMPUTATIONAL INVESTIGATION; COORDINATION SITES; ENANTIO; HIGH ACTIVATION ENERGY; HYDROVINYLATION; INDUCTION PERIODS; NICKEL HYDRIDES; QUANTITATIVE YIELDS; REGIO-SELECTIVE; THEORETICAL INVESTIGATIONS; TRANS EFFECT; TRANSFER STAGES; TRANSITION STATE;

EID: 67449149978     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900045p     Document Type: Article
Times cited : (42)

References (59)
  • 1
    • 0041378064 scopus 로고    scopus 로고
    • For a history of the reaction, a proposed mechanism, the scope, and its limitations, see: a
    • For a history of the reaction, a proposed mechanism, the scope, and its limitations, see: (a) RajanBabu, T. V. Chem. Rev. 2003, 103, 2845.
    • (2003) Chem. Rev , vol.103 , pp. 2845
    • RajanBabu, T.V.1
  • 7
    • 0033592173 scopus 로고    scopus 로고
    • Use of Wilke's Azaphospholene (L1): (a) Wegner, A.; Leitner, W. Chem. Commun. 1999, 1583, and references therein.
    • Use of Wilke's Azaphospholene (L1): (a) Wegner, A.; Leitner, W. Chem. Commun. 1999, 1583, and references therein.
  • 8
    • 0033610498 scopus 로고    scopus 로고
    • Phospholanes as ligands: (b) Nandi, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899.
    • Phospholanes as ligands: (b) Nandi, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899.
  • 10
    • 0037028566 scopus 로고    scopus 로고
    • Phosphiniates: (d) Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734.
    • Phosphiniates: (d) Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734.
  • 11
    • 0037028545 scopus 로고    scopus 로고
    • Phosphoramidites: (e) Franció, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736.
    • Phosphoramidites: (e) Franció, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736.
  • 16
    • 85026875962 scopus 로고    scopus 로고
    • Details of preparative methods: Smith, C. R.; Zhang, A.; Mans, D. J.; RajanBabu, T. V. Org. Synth. 2008, 85, 248.
    • (j) Details of preparative methods: Smith, C. R.; Zhang, A.; Mans, D. J.; RajanBabu, T. V. Org. Synth. 2008, 85, 248.
  • 21
    • 0041497161 scopus 로고
    • Chem. Abstr. 1979, 90, 6002.
    • (1979) Chem. Abstr , vol.90 , pp. 6002
  • 23
    • 0041497160 scopus 로고
    • Chem. Abstr. 1980, 93, 203573.
    • (1980) Chem. Abstr , vol.93 , pp. 203573
  • 27
    • 84868988143 scopus 로고    scopus 로고
    • DiRenzo, G. M. Mechanistic Studies of Catalytic Olefin Dimerization Reactions Using Electrophilicη3-allyl-Palladium(II) Complexes, Ph.D. Thesis University of North Carolina, 1997. We thank Professor Brookhart and Dr. DiRenzo for a copy of this dissertation
    • 3-allyl-Palladium(II) Complexes, Ph.D. Thesis University of North Carolina, 1997. We thank Professor Brookhart and Dr. DiRenzo for a copy of this dissertation.
  • 32
    • 67449129307 scopus 로고    scopus 로고
    • Frisch, M. J.; et al. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003 (See Supporting Information for a complete list of authors).
    • Frisch, M. J.; et al. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003 (See Supporting Information for a complete list of authors).
  • 33
    • 67449165698 scopus 로고    scopus 로고
    • We have also checked the effect of diffuse functions, as per the suggestion of one of the referees, on the energetics of two important steps at B3LYP/6-31, G*//B3LYP/6-31G* (and also at B3LYP/6-31, G*; given in parentheses below, The energy difference for 40 viz, 40S, 40R [vide infra, see text] changes from, 0.6 kcal/mol to, 0.5, 0.6) kcal/mol in the same direction. So is the case for 99, viz, 99RS, 99RR, which is now, 0.4 (0.3) kcal/mol versus the previous, 0.6 kcal/mol. The new activation energy for initiation is 19.2 (18.6) kcal/mol for S versus the earlier 18.8 kcal/mol, and for R 19.8 (19.2) kcal/mol versus the earlier 19.5 kcal/mol. The activation energy, 99RS, 86R, of the catalytic cycle is now
    • *; given in parentheses below). The energy difference for 40 viz., 40S - 40R [vide infra, see text] changes from - 0.6 kcal/mol to - 0.5 (-0.6) kcal/mol in the same direction. So is the case for 99, viz., 99RS - 99RR, which is now - 0.4 (0.3) kcal/mol versus the previous - 0.6 kcal/mol. The new activation energy for initiation is 19.2 (18.6) kcal/mol for S versus the earlier 18.8 kcal/mol, and for R 19.8 (19.2) kcal/mol versus the earlier 19.5 kcal/mol. The activation energy, 99RS - 86R, of the catalytic cycle is now
  • 36
    • 67449169199 scopus 로고    scopus 로고
    • This conformational search was carried out using the known bonding pattern of the system, which has only the usual chemical bonds; thus the search involved rotation across the bonds. A number of conformers of very close energy to the lowest conformer exist for many of the points in Figure 2. These were ignored from consideration for the discussion, although they are also populated
    • This conformational search was carried out using the known bonding pattern of the system, which has only the usual chemical bonds; thus the search involved rotation across the bonds. A number of conformers of very close energy to the lowest conformer exist for many of the points in Figure 2. These were ignored from consideration for the discussion, although they are also populated.
  • 37
    • 22944469409 scopus 로고    scopus 로고
    • For a recent DFT study
    • (a) For a recent DFT study: Ariafard, A.; Lin, Z. Organometallics 2005, 24, 3800.
    • (2005) Organometallics , vol.24 , pp. 3800
    • Ariafard, A.1    Lin, Z.2
  • 38
    • 33847089848 scopus 로고
    • For previous theoretical studies of bonding in allyl systems, see: b
    • For previous theoretical studies of bonding in allyl systems, see: (b) Albright, T. A.; Hofmann, P.; Hoffmann, R. J. Am. Chem. Soc. 1977, 99, 7546.
    • (1977) J. Am. Chem. Soc , vol.99 , pp. 7546
    • Albright, T.A.1    Hofmann, P.2    Hoffmann, R.3
  • 40
    • 0003625966 scopus 로고
    • Wilkinson, G, Ed, Pergamon: Oxford, England, Chapter 19, pp
    • (d) Mingos, D. M. P. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon: Oxford, England, 1982; Vol. 3, Chapter 19, pp 60-67.
    • (1982) Comprehensive Organometallic Chemistry , vol.3 , pp. 60-67
    • Mingos, D.M.P.1
  • 43
    • 0028442268 scopus 로고    scopus 로고
    • Allyl rotation mechanism in Ni(II) complexes: (b) Hampton, P. D.; Wu, S.; Alam, T. M.; Claverie, J. P. Organometallics 1994, 13, 2066.
    • Allyl rotation mechanism in Ni(II) complexes: (b) Hampton, P. D.; Wu, S.; Alam, T. M.; Claverie, J. P. Organometallics 1994, 13, 2066.
  • 46
    • 67449156789 scopus 로고    scopus 로고
    • 18 is slightly lower than 17 in energy without ZPE correction.
    • 18 is slightly lower than 17 in energy without ZPE correction.
  • 47
    • 67449129230 scopus 로고    scopus 로고
    • Pentacoordinate Ni-intermediates have been implicated in C, C coupling reactions and reductive eliminations, see: (a) Shultz, C. S, DeSimone, J. M, Brookhart, M. J. Am. Chem. Soc. 2001, 123, 9172
    • Pentacoordinate Ni-intermediates have been implicated in C - C coupling reactions and reductive eliminations, see: (a) Shultz, C. S.; DeSimone, J. M.; Brookhart, M. J. Am. Chem. Soc. 2001, 123, 9172.
  • 49
    • 84868991798 scopus 로고    scopus 로고
    • It may be noted that the transition state 34 is very much lower in energy than isoelectronic analogues, for example, tetrahedral 10 (Scheme 6, whereη3-allyl was not flexible enough to make room for the ligand substituents as in 34, which may be considered as a trigonal pyramid (rather than tetrahedral, with olefin in the plane of P and O Scheme 12
    • 3-allyl was not flexible enough to make room for the ligand substituents as in 34, which may be considered as a trigonal pyramid (rather than tetrahedral), with olefin in the plane of P and O (Scheme 12).
  • 50
    • 0031020614 scopus 로고    scopus 로고
    • For a similar result in the computational studies of Ni(II)-catalyzed polymerization/oligomerization of ethylene, see: (a) Deng, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 1094.
    • For a similar result in the computational studies of Ni(II)-catalyzed polymerization/oligomerization of ethylene, see: (a) Deng, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 1094.
  • 54
    • 67449129156 scopus 로고    scopus 로고
    • See also ref 21
    • (e) See also ref 21.
  • 57
    • 20444468574 scopus 로고    scopus 로고
    • For a review on C, H, πhydrogen bonds in organic reactions, see
    • For a review on C - H - πhydrogen bonds in organic reactions, see: Nishio, M. Tetrahedron 2005, 61, 6923.
    • (2005) Tetrahedron , vol.61 , pp. 6923
    • Nishio, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.