848609-02-9Relevant articles and documents
Rational electronic tuning of CBS catalyst for highly enantioselective borane reduction of trifluoroacetophenone
Korenaga, Toshinobu,Nomura, Kenji,Onoue, Kazutaka,Sakai, Takashi
supporting information; experimental part, p. 8624 - 8626 (2011/01/03)
α,α,α-Trifluoroacetophenone (2), which is susceptible to noncatalytic reduction by BH3, could be reduced to chiral alcohol up to 90% ee by using electronically tuned-CBS catalyst (1) with BH3. The enantioselectivities highly correlated with the differential orbital energies between 1-BH3 adduct and 2, which were calculated by DFT method.
Polyfluoroorganoboron-oxygen compounds. 4 [1] lithium pentafluorophenyltrimethoxyborate, Li[C6F5B(OMe) 3], reactions with selected electrophiles and nucleophiles
Adonin, Nicolay Yu.,Bardin, Vadim V.,Floerke, Ulrich,Frohn, Hermann-Josef
, p. 2638 - 2646 (2008/10/09)
Li[C6F5B(OMe)3] (1a) reacted with the electrophiles CD3C(O)CD3, CH3OD, CD 3CN, CH3CN, HOC2H4OH, Br 2, and I2 to give C6F5X (X = D, H, Br, I). The treatment of 1a with Me3SiCl or BF3 in CH 2Cl2 and CCl3F or pentene resulted in C 6F5B(OMe)2 or C6F5BF 2, respectively. The attempted metathesis of 1a with KF or [Bu 4N]Br in CH2Cl2 led to a mixture of M[(C 6F5)2B(OMe)2] (2b,c, main product) and M[C6F5B(OMe)3] (1b,c, minor product) (M = [Bu4N], K). Even in the presence of diethyl ether, THF, DME, or TMEDA salt 1a underwent dismutation to the diarylborate salt [Li(L) n][(C6F5)2B(OMe)2] (L = Et2O, THF, DME, TMEDA) and [Li(L)n][B(OMe)4]. In subsequent reactions with aqueous K[HF2] or [Bu 4N][HF2] M[(C6F5) 2B(OMe)2] (M = K, [Bu4N], [Li(L)n]) yielded K[(C6F5)2BF2] (4c) or [Bu4N][(C6F5)2BF2] (4b). The molecular structure of [Li·TMEDA][(C6F5) 2B(OMe)2] from single crystals showed significant cation-oxygen interactions.