Palladium-catalyzed insertion of alkynes into the Sn-B bond of a 2-stannyl-2,3-dihydro-1H-1,3,2-diazaborole and X-ray structure analyses of 1,3-di-tert-butyl-2[(Z)-2-phenyl-2-trimethylstannylethenyl]-2,3-dihydro- 1H-1,3,2-diazaborole and 1,3-di-tert-butyl-2[(Z)-1-ethyl-2-phenyl-2-trimethylstannylethenyl]-2,3- dihydro-1H-1,3,2-diazaborole

Weber L, Wartig HB, Stammler H-G, Stammler A, Neumann B (2000)
Organometallics 19(15): 2891-2895.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Reaction of equimolar amounts of 1,3-di-tert-butyl-2-trimethylstannyl-2,3-dihydro-1H,3,2-diazaborole (1) with a series of alkynes R-1-C equivalent to C-R-2 (2)(a: R-1 = H, R-2 = Ph; b: H, 4-ClC6H4; c: H, 4-BrC6H4; d: Ph, Ph; e: Me, Ph; f: Et, Ph; g: H, n-C4H9; h: Et, Et; i: H, n-C6H13) in the presence of a catalytic amount of [Pd(PPh3)(4)] (2 mol %) regioselectively afforded high yields of the alkenes (Z)-R-1[B]C=C(R-2)SnMe3 (3a-h) ([B] = tBuNCH=CHN(tBu)B] as the result of a cis-addition of the BSn bond of 1 to the acetylenic triple bond of 2. Spectroscopic evidence and X-ray structural analyses of 3a and 3f revealed that the bulky borolyl unit was added to the least sterically hindered end of the CC multiple bond.
Erscheinungsjahr
2000
Zeitschriftentitel
Organometallics
Band
19
Ausgabe
15
Seite(n)
2891-2895
ISSN
0276-7333
eISSN
1520-6041
Page URI
https://pub.uni-bielefeld.de/record/1619409

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Weber L, Wartig HB, Stammler H-G, Stammler A, Neumann B. Palladium-catalyzed insertion of alkynes into the Sn-B bond of a 2-stannyl-2,3-dihydro-1H-1,3,2-diazaborole and X-ray structure analyses of 1,3-di-tert-butyl-2[(Z)-2-phenyl-2-trimethylstannylethenyl]-2,3-dihydro- 1H-1,3,2-diazaborole and 1,3-di-tert-butyl-2[(Z)-1-ethyl-2-phenyl-2-trimethylstannylethenyl]-2,3- dihydro-1H-1,3,2-diazaborole. Organometallics. 2000;19(15):2891-2895.
Weber, L., Wartig, H. B., Stammler, H. - G., Stammler, A., & Neumann, B. (2000). Palladium-catalyzed insertion of alkynes into the Sn-B bond of a 2-stannyl-2,3-dihydro-1H-1,3,2-diazaborole and X-ray structure analyses of 1,3-di-tert-butyl-2[(Z)-2-phenyl-2-trimethylstannylethenyl]-2,3-dihydro- 1H-1,3,2-diazaborole and 1,3-di-tert-butyl-2[(Z)-1-ethyl-2-phenyl-2-trimethylstannylethenyl]-2,3- dihydro-1H-1,3,2-diazaborole. Organometallics, 19(15), 2891-2895. doi:10.1021/om000042w
Weber, L., Wartig, H. B., Stammler, H. - G., Stammler, A., and Neumann, B. (2000). Palladium-catalyzed insertion of alkynes into the Sn-B bond of a 2-stannyl-2,3-dihydro-1H-1,3,2-diazaborole and X-ray structure analyses of 1,3-di-tert-butyl-2[(Z)-2-phenyl-2-trimethylstannylethenyl]-2,3-dihydro- 1H-1,3,2-diazaborole and 1,3-di-tert-butyl-2[(Z)-1-ethyl-2-phenyl-2-trimethylstannylethenyl]-2,3- dihydro-1H-1,3,2-diazaborole. Organometallics 19, 2891-2895.
Weber, L., et al., 2000. Palladium-catalyzed insertion of alkynes into the Sn-B bond of a 2-stannyl-2,3-dihydro-1H-1,3,2-diazaborole and X-ray structure analyses of 1,3-di-tert-butyl-2[(Z)-2-phenyl-2-trimethylstannylethenyl]-2,3-dihydro- 1H-1,3,2-diazaborole and 1,3-di-tert-butyl-2[(Z)-1-ethyl-2-phenyl-2-trimethylstannylethenyl]-2,3- dihydro-1H-1,3,2-diazaborole. Organometallics, 19(15), p 2891-2895.
L. Weber, et al., “Palladium-catalyzed insertion of alkynes into the Sn-B bond of a 2-stannyl-2,3-dihydro-1H-1,3,2-diazaborole and X-ray structure analyses of 1,3-di-tert-butyl-2[(Z)-2-phenyl-2-trimethylstannylethenyl]-2,3-dihydro- 1H-1,3,2-diazaborole and 1,3-di-tert-butyl-2[(Z)-1-ethyl-2-phenyl-2-trimethylstannylethenyl]-2,3- dihydro-1H-1,3,2-diazaborole”, Organometallics, vol. 19, 2000, pp. 2891-2895.
Weber, L., Wartig, H.B., Stammler, H.-G., Stammler, A., Neumann, B.: Palladium-catalyzed insertion of alkynes into the Sn-B bond of a 2-stannyl-2,3-dihydro-1H-1,3,2-diazaborole and X-ray structure analyses of 1,3-di-tert-butyl-2[(Z)-2-phenyl-2-trimethylstannylethenyl]-2,3-dihydro- 1H-1,3,2-diazaborole and 1,3-di-tert-butyl-2[(Z)-1-ethyl-2-phenyl-2-trimethylstannylethenyl]-2,3- dihydro-1H-1,3,2-diazaborole. Organometallics. 19, 2891-2895 (2000).
Weber, Lothar, Wartig, Henning B., Stammler, Hans-Georg, Stammler, Anja, and Neumann, Beate. “Palladium-catalyzed insertion of alkynes into the Sn-B bond of a 2-stannyl-2,3-dihydro-1H-1,3,2-diazaborole and X-ray structure analyses of 1,3-di-tert-butyl-2[(Z)-2-phenyl-2-trimethylstannylethenyl]-2,3-dihydro- 1H-1,3,2-diazaborole and 1,3-di-tert-butyl-2[(Z)-1-ethyl-2-phenyl-2-trimethylstannylethenyl]-2,3- dihydro-1H-1,3,2-diazaborole”. Organometallics 19.15 (2000): 2891-2895.