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Volumn 46, Issue 31, 2007, Pages 5929-5933

Definitive evidence for the insertion of terminal alkynes into ArylS-Pt bonds: "o-halogen effect" in stoichiometric and catalytic reactions

Author keywords

Alkynes; Insertion; Neighboring group effects; Platinum; S ligands

Indexed keywords

ADDITION REACTIONS; CATALYST ACTIVITY; LIGANDS; PLATINUM;

EID: 34547801790     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604986     Document Type: Article
Times cited : (46)

References (57)
  • 1
    • 0009641346 scopus 로고    scopus 로고
    • For reviews, see: a, Eds, A. Togni, H. Grützmacher, Wiley-VCH, Weinheim
    • For reviews, see: a) H. Kuniyasu in Catalytic Heterofunctionalization (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, p. 217;
    • (2001) Catalytic Heterofunctionalization , pp. 217
    • Kuniyasu, H.1
  • 3
    • 14744290401 scopus 로고    scopus 로고
    • Eds, H. Yamamoto, K. Oshima, Wiley-VCH, Weinheim
    • c) A. Ogawa, Main Group Metals in Organic Synthesis (Eds.: H. Yamamoto, K. Oshima), Wiley-VCH, Weinheim,2004, p. 813;
    • (2004) Main Group Metals in Organic Synthesis , pp. 813
    • Ogawa, A.1
  • 14
    • 0000417550 scopus 로고    scopus 로고
    • T. Ishiyama, K. Nishijima, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 7219; 9-BBN = 9-borabicyclo[3.3.1]nonane.
    • T. Ishiyama, K. Nishijima, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 7219; 9-BBN = 9-borabicyclo[3.3.1]nonane.
  • 28
    • 34547727249 scopus 로고    scopus 로고
    • In the following discussion, cis and trans refer to the relationship of the two PPh3 groups at a Pt center; E and Z refer to the configuration of the double bond of a vinyl substituent
    • 3 groups at a Pt center; E and Z refer to the configuration of the double bond of a vinyl substituent.
  • 32
    • 0037474822 scopus 로고    scopus 로고
    • n] (n = 1,2) was described recently; however, no clear information about the insertion step was provided: a) V. P. Ananikov, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko, Organometallics 2003, 22, 1414;
    • n] (n = 1,2) was described recently; however, no clear information about the insertion step was provided: a) V. P. Ananikov, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko, Organometallics 2003, 22, 1414;
  • 34
    • 0035982968 scopus 로고    scopus 로고
    • The use of 1,2-bis(diphenylphosphanyl)ethane (dppe) as a ligand and dimethyl acetylenedicarboxylate (DMAD) as the alkyne enabled the direct observation of insertion into a S-Pd bond: K. Sugoh, H. Kuniyasu, H. Kurosawa, Chem. Lett. 2002, 106.
    • The use of 1,2-bis(diphenylphosphanyl)ethane (dppe) as a ligand and dimethyl acetylenedicarboxylate (DMAD) as the alkyne enabled the direct observation of insertion into a S-Pd bond: K. Sugoh, H. Kuniyasu, H. Kurosawa, Chem. Lett. 2002, 106.
  • 37
    • 34547804784 scopus 로고    scopus 로고
    • CCDC-610343 (5a), CCDC-610574 (4i), CCDC-639788 (cis-10), and CCDC-639789 (trans-10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • CCDC-610343 (5a), CCDC-610574 (4i), CCDC-639788 (cis-10), and CCDC-639789 (trans-10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 38
    • 0001050480 scopus 로고    scopus 로고
    • For the insertion of activated terminal alkynes into S-M bonds (M = Mo, Co, Ru, W, Fe, Rh, Ir), see: a) T. R. Halbert, W. H. Pan, E. I. Stiefel, J. Am. Chem. Soc. 1983, 105, 5476;
    • For the insertion of activated terminal alkynes into S-M bonds (M = Mo, Co, Ru, W, Fe, Rh, Ir), see: a) T. R. Halbert, W. H. Pan, E. I. Stiefel, J. Am. Chem. Soc. 1983, 105, 5476;
  • 43
    • 33751156297 scopus 로고
    • For the insertion of terminal alkynes into S-Ru and S-Rh bonds, see: a
    • For the insertion of terminal alkynes into S-Ru and S-Rh bonds, see: a) U. Koelle, C. Rietmann, J. Tjoe, T. Wagner, U. Englert, Organometallics 1995, 14, 703;
    • (1995) Organometallics , vol.14 , pp. 703
    • Koelle, U.1    Rietmann, C.2    Tjoe, J.3    Wagner, T.4    Englert, U.5
  • 45
    • 0032537966 scopus 로고    scopus 로고
    • II complex to form a C-S bond: G. Mann, D. Baranano, J. F. Hartwig, A. L. Rheingold, I. A. Guzei, J. Am. Chem. Soc. 1998, 120, 9205.
    • II complex to form a C-S bond: G. Mann, D. Baranano, J. F. Hartwig, A. L. Rheingold, I. A. Guzei, J. Am. Chem. Soc. 1998, 120, 9205.
  • 49
    • 32844470775 scopus 로고    scopus 로고
    • Intramolecular coordination of the β cis SAr group of an αβ-unsaturated thioester facilitated decarbonylation: T. Kato, H. Kuniyasu, T. Kajiura, Y. Minami, A. Ohtaka, M. Kinomoto, J. Terao, H. Kurosawa, N. Kambe, Chem. Commun. 2006, 868.
    • Intramolecular coordination of the β cis SAr group of an αβ-unsaturated thioester facilitated decarbonylation: T. Kato, H. Kuniyasu, T. Kajiura, Y. Minami, A. Ohtaka, M. Kinomoto, J. Terao, H. Kurosawa, N. Kambe, Chem. Commun. 2006, 868.
  • 50
    • 0001426851 scopus 로고    scopus 로고
    • Assistance through the intramolecular coordination of an OH group has been reported on the basis of a molecular-orbital study of the insertion of an alkyne into a B-Pt bond: Q. Cui, D. G. Musaev, K. Morokuma, Organometallics 1997, 16, 1355
    • Assistance through the intramolecular coordination of an OH group has been reported on the basis of a molecular-orbital study of the insertion of an alkyne into a B-Pt bond: Q. Cui, D. G. Musaev, K. Morokuma, Organometallics 1997, 16, 1355.
  • 51
    • 34547812072 scopus 로고    scopus 로고
    • The configurations of trans-10 and cis-10 were identified unambiguously by X-ray crystallographic analysis: R. D. Lai, A. Shaver, Inorg. Chem. 1981, 20, 411.
    • The configurations of trans-10 and cis-10 were identified unambiguously by X-ray crystallographic analysis: R. D. Lai, A. Shaver, Inorg. Chem. 1981, 20, 411.
  • 52
    • 0034653692 scopus 로고    scopus 로고
    • An authentic sample of cis-11, which isomerizes to thermodynamically more stable trans-11, was synthesized by oxidative addition of the corresponding vinyl sulfide to [Pt(PPh 3)2C2H4, H. Kuniyasu, A. Ohtaka, T. Nakazono, M. Kinomoto, H. Kurosawa, J. Am. Chem. Soc. 2000, 122, 2375
    • 4)]: H. Kuniyasu, A. Ohtaka, T. Nakazono, M. Kinomoto, H. Kurosawa, J. Am. Chem. Soc. 2000, 122, 2375.
  • 53
    • 34547795240 scopus 로고    scopus 로고
    • 0 complex probably occurred via the divinyl platinum complex. See the discussion about the possible course of reactions of platinum dithiolates with alkynes in reference [4b].
    • 0 complex probably occurred via the divinyl platinum complex. See the discussion about the possible course of reactions of platinum dithiolates with alkynes in reference [4b].
  • 57
    • 34547792899 scopus 로고    scopus 로고
    • The cis vinyl platinum complex was also detected as a kinetic product in the early stages of the reaction of 4i with 2a.
    • The cis vinyl platinum complex was also detected as a kinetic product in the early stages of the reaction of 4i with 2a.


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