Synthesis and characterization of a doubly base-stabilized B 3H6+ analogue
The answer to an old question: A doubly base-stabilized B3H 6+ analogue (see structure: B green, C gray, N blue, H light gray, H on C not shown) has been synthesized and completely characterized. Quantum-chemical calculations on a simplified model confirmed the presence of closed B-B-B three-center bonding and σ-aromatic character. Copyright
In an attempt to prepare the heavier analogue of NHC-stabilized borenium cation, we have prepared a silylene-coordinated borenium equivalent (1a), which can be viewed as a contact ion pair of borenium and triflate. The triflate anion coordinates to the oxophilic silicon center, leaving the boron center existing in a trigonal-planar geometry in the solid state and in solution. Nucleophilic substitution reactions of 1a all result in the release of free silylene ligand, demonstrating the borenium-ion-like reactivity of 1a. Chemical reduction of 1a leads to a neutral radical possessing a partial Si-B double bond.
Regio- and Stereoselective Cross-aldol Reactions via Dialkylboryl Triflates
New borylating reagents, (Bu2BOTf and 9-BBNOTf), were prepared in high yields.The triflates reacted with enolizable ketones in the presence of tertiary amines to generate selectively one of the regioisomers of vinyloxyboranes by the choice of the reagents (the dialkylboryl triflates and tertiary amines) under mild reaction conditions.Vinyloxyboranes thus generated showed remarkable reactivity toward aldehydes to give only one regioisomer of the corresponding cross-aldols in good yields.High stereoselectivity was also observed in these reactions.
Inoue, Tan,Mukaiyama, Teruaki
p. 174 - 178
(2007/10/02)
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