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.

Journal Article | Published | English

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Abstract
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.
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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.
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.
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