o-[(Dimesitylboryl)phenyl]dimethylsilane (1a) undergoes dehydrogenative condensation with alcohols and amines, giving the corresponding alkoxysilanes 4–7 and aminosilanes 8 and 9 in moderate to high yields. It is plausible that the ortho-boryl group in 1a electrophilically activates the Si–H bond.
o-(Hydroxydimethylsilyl)(dimesitylboryl)benzene (1) underwent intramolecular cyclization to give 5,5dimesityl-2,2-dimethyl-3,4-benzo-1,2,5-oxasilaboracyclopentene (4) and mesitylene by boron-aryl bond cleavage. Whereas triethylamine as an additive accelerated the cyclization, DBU stabilized a silyloxyborate complex, 1,8-diazabicyclo[5.4.0]-7-undecenium 5,5-dimesityl-2,2-dimethyl-3,4-benzo-1,2,5-oxasilaboratacyclopentene, which was characterized by X-ray crystallographic analysis and HF calculations. The deuterium-labeling experiments revealed that the hydrogen migrated from the hydroxyl group in 1 to the leaving mesitylene.
Organo-silicon compounds S 0060Dehydrogenative Condensation of (o-Borylphenyl)hydrosilane with Alcohols and Amines. -Title compound (I) undergoes dehydrogenative condensation with alcohols (II) and amines (IV) to give the corresponding alkoxy and amino silanes (III) and (V), respectively. Electrophilic activation of the Si-H bond by the ortho-boryl group is assumed to render the silicon center in (I) susceptible to nucleophilic attack by alcohols (II) and amines (IV). -(KAWACHI*, A.; ZAIMA, M.; TANI, A.; YAMAMOTO, Y.; Chem. Lett. 36 (2007) 3, 362-363; Dep. Chem., Grad. Sch. Sci., Hiroshima Univ., Higashi-Hiroshima 739, Japan; Eng.) -M. Paetzel 32-180
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