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Volumn 55, Issue 6, 1990, Pages 1857-1867

Palladium- and Molybdenum-Catalyzed Hydrostannation of Alkynes. A Novel Access to Regio- and Stereodefined Vinylstannanes

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EID: 0040746033     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00293a035     Document Type: Article
Times cited : (492)

References (115)
  • 4
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    • Electrophiles used in palladium-catalyzed condensation reactionslb,c include acyl chlorides, allyl halides, vinyl halides and triflates, aryl halides and triflates, vinyl epoxides and perfluoroalkyl iodides
    • Aryl halides
    • Electrophiles used in palladium-catalyzed condensation reactionslb,c include acyl chlorides, allyl halides, vinyl halides and triflates, aryl halides and triflates, vinyl epoxides and perfluoroalkyl iodides. For very recent references, see the following. Vinyl halides: (a) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987,109, 813. Aryl halides:
    • (1987) J. Am. Chem. Soc. , vol.109 , Issue.813
    • Stille, J.K.1    Groh, B.L.2
  • 37
    • 0000672350 scopus 로고
    • After this work was well underway, two short communications appeared dealing, respectively, with palladium-catalyzed and with rhodium-catalyzed hydrostannation reactions
    • After this work was well underway, two short communications appeared dealing, respectively, with palladium-catalyzed and with rhodium-catalyzed hydrostannation reactions: Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468.
    • (1987) Bull. Chem. Soc. Jpn. , vol.60 , pp. 3468
    • Ichinose, Y.1    Oda, H.2    Oshima, K.3    Utimoto, K.4
  • 62
    • 85023834574 scopus 로고    scopus 로고
    • In the absence of acetylenic compounds, an orange solution of 3 in THF under argon atmosphere immediately turns black and cloudy upon addition of Bu3SnH
    • The tin byproduct of the reaction is Bu3SnBr (GC/MS). IR analysis (after dilution in CHCI3) shows a single strong CO absorption at 1950 cm-1. Thus, the species which forms is not the known (THF)3Mo(CO)3 (kc0 = 1920 and 1780 cm1. Hoff, C. D. J. Organomet. Chem. 1985, 282, 201). If the reaction of 3 and Bu3SnH is performed under CO atmosphere (in this case the solution turns red and stays homogeneous), the CO band at 1950 cm-1 is progressively replaced, over ca. 1 h, by the CO band at 1986 cm-1 of Mo(CO)6, which can be precipitated out of the solution quantitatively
    • In the absence of acetylenic compounds, an orange solution of 3 in THF under argon atmosphere immediately turns black and cloudy upon addition of Bu3SnH. NMR analysis (THF-d6) shows a complete disappearance of the proton signals20 of the 03BC-allyl entity. The tin byproduct of the reaction is Bu3SnBr (GC/MS). IR analysis (after dilution in CHCI3) shows a single strong CO absorption at 1950 cm-1. Thus, the species which forms is not the known (THF)3Mo(CO)3 (kc0 = 1920 and 1780 cm1. Hoff, C. D. J. Organomet. Chem. 1985, 282, 201). If the reaction of 3 and Bu3SnH is performed under CO atmosphere (in this case the solution turns red and stays homogeneous), the CO band at 1950 cm-1 is progressively replaced, over ca. 1 h, by the CO band at 1986 cm-1 of Mo(CO)6, which can be precipitated out of the solution quantitatively.
    • NMR analysis (THF-d6) shows a complete disappearance of the proton signals20 of the 03BC-allyl entity
  • 64
    • 85045815223 scopus 로고
    • Corrigendum: Tetrahedron Lett. 1988, 29, 3874.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 3874
  • 65
    • 0010682666 scopus 로고
    • Previous studies on palladium-catalyzed hydrostannolytic or hydrostannation reactions
    • Previous studies on palladium-catalyzed hydrostannolytic or hydrostannation reactions: Guibe, F.; Zigna, A. M.; Balavoine, G. J. Organomet. Chem. 1986, 306, 257.
    • (1986) J. Organomet. Chem. , vol.306 , Issue.257
    • Guibe, F.1    Zigna, A.M.2    Balavoine, G.3
  • 72
    • 11644311048 scopus 로고
    • The values of the ligand cone angle 6 for P(o-tolyl)3, PPh3, and P(OMe)3 are, respectively, 194
    • The values of the ligand cone angle 6 for P(o-tolyl)3, PPh3, and P(OMe)3 are, respectively, 194(Tolman, C. A. Chem. Rev. 1977, 77, 313.
    • (1977) Chem. Rev. , vol.77 , Issue.313
    • Tolman, C.A.1
  • 81
    • 85023840419 scopus 로고    scopus 로고
    • Simple bromoalkenes are not as reactive. For instance, under similar conditions and due to competitive tributyltin hydride decomposition, 1-bromostyrene is reduced only to the extent of ca
    • Simple bromoalkenes are not as reactive. For instance, under similar conditions and due to competitive tributyltin hydride decomposition, 1-bromostyrene is reduced only to the extent of ca. 50% by addition of one equivalent of tributyltin hydride (observations from this laboratory).
    • 50% by addition of one equivalent of tributyltin hydride (observations from this laboratory)
  • 89
    • 0038584404 scopus 로고
    • See, for instance, ref lb, 2d, 11 and the following
    • See, for instance, ref lb, 2d, 11 and the following: Piers, E.; Karumaratne, V. J. Org. Chem. 1983, 48, 1774.
    • (1983) J. Org. Chem. , vol.48 , pp. 1774
    • Piers, E.1    Karumaratne, V.2


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