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Lothar Weber, Daniel Eickhoff, Johannes Halama, Stefanie Werner, Jan Kahlert, Hans-Georg Stammler and Beate Neumann Hydroboration of Alkyne-Functionalized 1,3,2-Benzodiazaboroles European Journal of Inorganic Chemistry 2013

Article first published online: 20 MAR 2013 | DOI: 10.1002/ejic.201201489

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The hydroboration of the C≡C bond of a series of 2-alkynyl-1,3-diethyl-1,3,2-benzodiazaboroles R-C≡C-B(NEt)2C6H4 (R = nBu, tBu, Ph, pMe2NC6H4, pMeOC6H4) with dicyclohexylborane regioselectively afforded 1,1-diborylalkenes (Z)-R(H)C=C-{(B{NEt}2C6H4)BCy2}. Reaction of the trimethylsilyl-ethynyl derivative with HBCy2 yielded a 2.5:1 mixture of the 1,2- and 1,1-diborylated 2-alkenyl-benzodiazaboroles.

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