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Volumn 27, Issue 18, 2008, Pages 4788-4802

Insertion of alkynes into an ArS-Pt bond: Regio- and stereoselective thermal reactions, facilitation by "o-halogen effect" and photoirradiation, different alkyne preferences depending on the ancillary ligand, and application to a catalytic reaction

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYSIS; HYDROCARBONS;

EID: 53849148938     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800464y     Document Type: Article
Times cited : (40)

References (142)
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    • For C-C bond-forming reductive elimination from Pd(II) complexes, see: (a) Coliman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principle and Application of Organotransition Metal Chemistry, 2nd ed.; University Science Books: Mill Valley, CA, 1987; p 322.
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    • For C-S bond-forming reductive elimination from Pd(II) complexes, see:(a) Mann, G.; Baranano, D.; Hartwig, J. F.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1998, 120, 9205.
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    • The σ-bond metathesis between either 5 or 6 and 1 can also afford 3
    • The σ-bond metathesis between either 5 or 6 and 1 can also afford 3.
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    • The DFT study on the mechanism of Pd-catalyzed thioboration (G, 9-BBN6) of 2 proposed that 6 is yielded through bond metathesis between an S-B bond and an alkyne-coordinated C-Pd bond; see ref 15
    • 6) of 2 proposed that 6 is yielded through bond metathesis between an S-B bond and an alkyne-coordinated C-Pd bond; see ref 15.
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    • The insertions of activated 2 into S-M (M = Mo, Co, Ru, W, Fe, Rh, Ir, and Ru) bonds have been reported:(a) Halbert, T. R.; Pan, W. H.; Stiefel, E. I. J. Am. Chem. Soc. 1983, 105, 5476.
    • The insertions of activated 2 into S-M (M = Mo, Co, Ru, W, Fe, Rh, Ir, and Ru) bonds have been reported:(a) Halbert, T. R.; Pan, W. H.; Stiefel, E. I. J. Am. Chem. Soc. 1983, 105, 5476.
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    • The successive insertion into a S-Pd bond and following reductive elimination were indicated by the reaction of Pd(SAr)2(dppe) with DMAD dimethyl acetylenedicarboxylate, Sugoh, K, Kuniyasu, H, Kurosawa, H. Chem. Lett. 2002, 106
    • 2(dppe) with DMAD (dimethyl acetylenedicarboxylate): Sugoh, K.; Kuniyasu, H.; Kurosawa, H. Chem. Lett. 2002, 106.
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    • A part of the present study has been reported in communications: Kuniyasu, H.; Yamashita, F.; Terao, J.; Kambe, N. Angew. Chem., Int. Ed. Engl. 2007, 46, 5929. See also refs 10b and 10g.
    • A part of the present study has been reported in communications: Kuniyasu, H.; Yamashita, F.; Terao, J.; Kambe, N. Angew. Chem., Int. Ed. Engl. 2007, 46, 5929. See also refs 10b and 10g.
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    • 3 and other reagents has been confirmed during the course of the present study.
    • 3 and other reagents has been confirmed during the course of the present study.
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    • 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.
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    • w =0.113.
    • w =0.113.
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    • Crystal data for trans-Z-10A: space group P2 1/n, 14, a, 12.1258(2) Å, b= 12.6125(3) Å, c, 34.5793(7) Å, β= 100.5756(7)°, Z, 4, ρ, 1.54 g/cm3, R, 0.040, and Rw, 0.085. Crystal data for trans-Z-10e: space group Pna2 1/n, 33, a, 39.9145(7) Å, b, 11.9216(3) Å, c, 9.4584(2) Å, β, 101.6122(9)°, Z, 4, ρ, 1.542 g/cm 3, R, 0.040, and Rw, 0.118
    • w, = 0.118.
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    • Intramolecular coordination of a β-cis-SAr group of an α,β-unsaturated acyl platinum and palladium complexes facilitated decarbonylation: Kato, T.; Kuniyasu, H.; Kajiura, T.; Minami, Y.; Ohtaka, A.; Kinomoto, M.; Terao, J.; Kurosawa, H.; Kambe, N. Chem. Commun. 2006, 868.
    • Intramolecular coordination of a β-cis-SAr group of an α,β-unsaturated acyl platinum and palladium complexes facilitated decarbonylation: Kato, T.; Kuniyasu, H.; Kajiura, T.; Minami, Y.; Ohtaka, A.; Kinomoto, M.; Terao, J.; Kurosawa, H.; Kambe, N. Chem. Commun. 2006, 868.
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    • 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: Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1997, 16, 1355.
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    • 34
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    • For C-C bond-forming reductive elimination from Pt(II) complexes, see:(a) Stang, P. J.; Kowalski, M. H. J. Am. Chem. Soc 1989, 111, 3356.
    • For C-C bond-forming reductive elimination from Pt(II) complexes, see:(a) Stang, P. J.; Kowalski, M. H. J. Am. Chem. Soc 1989, 111, 3356.
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    • The configurations of trans-8 and cis-8 were independently identified by X-ray crystallographic analysis: Lai, R. D.; Shaver, A. Inorg. Chem. 1981, 20, 477.
    • The configurations of trans-8 and cis-8 were independently identified by X-ray crystallographic analysis: Lai, R. D.; Shaver, A. Inorg. Chem. 1981, 20, 477.
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    • 53849128145 scopus 로고    scopus 로고
    • 2 (7i) under similar reaction conditions did not take place at all.
    • 2 (7i) under similar reaction conditions did not take place at all.
  • 123
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    • The sample has to be strictly shielded to suppress the insertion because Z-16c was formed in 40% yield after 48 h with the sample placed under fluorescent light.
    • The sample has to be strictly shielded to suppress the insertion because Z-16c was formed in 40% yield after 48 h with the sample placed under fluorescent light.
  • 124
    • 53849134458 scopus 로고    scopus 로고
    • 3. This could rule out the possibility that the retardation was caused by forming the five-ligand-coordinated platinum complex.
    • 3. This could rule out the possibility that the retardation was caused by forming the five-ligand-coordinated platinum complex.
  • 126
    • 53849118772 scopus 로고    scopus 로고
    • Because cis-Z-16c hardly absorbs >430 run light, the cis-to-trans isomerization from cis-Z-16c was suppressed under the reaction conditions of entry 11. See the Supporting Information for the UV-vis spectra of trans-8a and cis-Z-16c.
    • Because cis-Z-16c hardly absorbs >430 run light, the cis-to-trans isomerization from cis-Z-16c was suppressed under the reaction conditions of entry 11. See the Supporting Information for the UV-vis spectra of trans-8a and cis-Z-16c.
  • 127
    • 53849117760 scopus 로고    scopus 로고
    • When a solution of 2n was treated with trans-8a under the irradiation of a UV(Hg) lamp (500 W), 8a was consumed within 10 min to yield 76% 16c (52% of cis-Z, 10% trans-Z, and 14% cis-E) together with undetermined byproducts.
    • When a solution of 2n was treated with trans-8a under the irradiation of a UV(Hg) lamp (500 W), 8a was consumed within 10 min to yield 76% 16c (52% of cis-Z, 10% trans-Z, and 14% cis-E) together with undetermined byproducts.
  • 128
    • 53849142523 scopus 로고    scopus 로고
    • 3 of 8a: Tebby, J. C.; Wilson, I. F.; Griffiths, D. V. J. Chem. Soc., Perkin Trans. 1 1976, 2133.
    • 3 of 8a: Tebby, J. C.; Wilson, I. F.; Griffiths, D. V. J. Chem. Soc., Perkin Trans. 1 1976, 2133.
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    • For photoirradiated ligand dissociation, see:a
    • For photoirradiated ligand dissociation, see:(a) Wada, M.; Kumazoe, M. J. Chem. Soc. Chem. Commun. 1985, 1204.
    • (1985) J. Chem. Soc. Chem. Commun , pp. 1204
    • Wada, M.1    Kumazoe, M.2
  • 137
    • 53849125404 scopus 로고    scopus 로고
    • The cis vinyl platinum complex was also detected as a kinetic product in the early stages of the reaction of 7j with 2a
    • The cis vinyl platinum complex was also detected as a kinetic product in the early stages of the reaction of 7j with 2a.
  • 138
    • 53849114640 scopus 로고    scopus 로고
    • 6.
    • 6.
  • 139
    • 53849141473 scopus 로고    scopus 로고
    • Crystal data for 27a: space group P1̄(#2, a, 12.631(1) Å, b, 17.188(2) Å, c= 11.455(1) Å, α, 90.219(4)°, β= 114.082(5)°, γ, 107.153(3)°, Z=I, ρ, 1.518 g/cm3, R, 0.028, Rw, 0.038
    • w = 0.038.
  • 140
    • 0001458913 scopus 로고    scopus 로고
    • It has been proposed that the insertion of CF2=CF2 into the O-Pt bond of Pt(OMe)(CH3)(dppe) proceeds via a similar five-ligand-coordinated complex; see:Bryndza, H. Organometallics 1985, 4, 406
    • 3)(dppe) proceeds via a similar five-ligand-coordinated complex; see:Bryndza, H. Organometallics 1985, 4, 406.
  • 141
    • 53849130267 scopus 로고    scopus 로고
    • w = 0.117.
    • w = 0.117.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.