期刊
DALTON TRANSACTIONS
卷 46, 期 7, 页码 2263-2269出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6dt04649e
关键词
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资金
- Academy of Finland [139550, 276586]
- Hungarian NKFI Grant [K-115660]
- COST action [CM0905]
- Academy of Finland (AKA) [276586] Funding Source: Academy of Finland (AKA)
2-(Dialkylamino) phenylboranes containing the BXZ group, where X, Z = C6F5, Cl, and H, were prepared in a few synthetic steps and demonstrated the cleavage of H-2 under mild conditions. Depending on the nature of the dialkylamino group, X, and Z, the stability of the produced zwitterionic H-2 adducts varies from isolated solids indefinitely stable in an inert atmosphere to those quickly equilibrating with the initial aminoborane and H-2. Using a combined experimental/computational approach on a series of isostructural aminoboranes (dialkylamino = 2,2,6,6-tetramethylpiperid-1-yl), it was demonstrated that the electro-negativity and the steric effect of the substituents generally follow the trend C6F5 similar to Cl >> H. This observation is useful for designing new FLPs for practical applications. As an example, we demonstrated the hydrogenation of alkynes to cis-alkenes under mild conditions that was catalyzed by a chloro-analogue of the C6F5-substituted aminoborane developed previously. The presence of a BHCl group in the amino-chloroboranes or in their H-2 adducts features facile redistribution of the H and Cl atoms and the formation of polychloro and polyhydrido species.
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