Hydroboration of Alkyne-Functionalized 1,3,2-Benzodiazaboroles

Weber L, Eickhoff D, Halama J, Werner S, Kahlert J, Stammler H-G, Neumann B (2013)
European Journal of Inorganic Chemistry 2013(14): 2608-2614.

Journal Article | Published | English

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Abstract
Reactions of equimolar amounts of dicyclohexylborane (DCB) with a series of 2-alkynyl-1,3-diethyl-1,3,2-benzodiazaboroles RCCB(NEt)2C6H4 (1: R = nBu, 2: R = tBu, 3: R = Ph, 4: R = p-Me2NC6H4, 5: R = p-MeOC6H4) regioselectively afforded the 1,1-diborylalkenes (Z)-R(H)C=C{(B{NEt}2C6H4)B(c-C6H11)2} (7a11a) as the result of a cis-addition of the BH bond of the borane to the CC triple bond in compounds 1 to 5. In contrast to this, reaction of Me3SiCCB(NEt)2C6H4 (6) with HB(c-C6H11)2 yielded a 2.5:1 mixture of the 1,2-diborylated alkene (Z)-Me3Si{(c-C6H11)2B}C=CHB(NEt)2C6H4 (12b) and the 1,1-regioisomer (Z)-Me3Si(H)C=C{B(NEt)2C6H4}{B(c-C6H11)2} (12a). These results were rationalized by the differing -acceptor qualities of the benzodiazaborolyl and trimethylsilyl substituents at the CC triple bond in compounds 1 to 6. The novel products 712 were characterized by elemental analysis, mass spectrometry and NMR spectroscopy (1H, 11B, and 13C NMR). The molecular structures of 9b and 12b were substantiated by single-crystal X-ray diffraction analysis.
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Weber L, Eickhoff D, Halama J, et al. Hydroboration of Alkyne-Functionalized 1,3,2-Benzodiazaboroles. European Journal of Inorganic Chemistry. 2013;2013(14):2608-2614.
Weber, L., Eickhoff, D., Halama, J., Werner, S., Kahlert, J., Stammler, H. - G., & Neumann, B. (2013). Hydroboration of Alkyne-Functionalized 1,3,2-Benzodiazaboroles. European Journal of Inorganic Chemistry, 2013(14), 2608-2614.
Weber, L., Eickhoff, D., Halama, J., Werner, S., Kahlert, J., Stammler, H. - G., and Neumann, B. (2013). Hydroboration of Alkyne-Functionalized 1,3,2-Benzodiazaboroles. European Journal of Inorganic Chemistry 2013, 2608-2614.
Weber, L., et al., 2013. Hydroboration of Alkyne-Functionalized 1,3,2-Benzodiazaboroles. European Journal of Inorganic Chemistry, 2013(14), p 2608-2614.
L. Weber, et al., “Hydroboration of Alkyne-Functionalized 1,3,2-Benzodiazaboroles”, European Journal of Inorganic Chemistry, vol. 2013, 2013, pp. 2608-2614.
Weber, L., Eickhoff, D., Halama, J., Werner, S., Kahlert, J., Stammler, H.-G., Neumann, B.: Hydroboration of Alkyne-Functionalized 1,3,2-Benzodiazaboroles. European Journal of Inorganic Chemistry. 2013, 2608-2614 (2013).
Weber, Lothar, Eickhoff, Daniel, Halama, Johannes, Werner, Stefanie, Kahlert, Jan, Stammler, Hans-Georg, and Neumann, Beate. “Hydroboration of Alkyne-Functionalized 1,3,2-Benzodiazaboroles”. European Journal of Inorganic Chemistry 2013.14 (2013): 2608-2614.
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