The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature. HPLC of Formula: C10H19NO3, 143900-44-1, Name is (S)-tert-Butyl 3-hydroxypiperidine-1-carboxylate, SMILES is O=C(N1C[C@@H](O)CCC1)OC(C)(C)C, in an article , author is Zhou, Miaomiao, once mentioned of 143900-44-1.
Dual reactivity of B(C6F5)(3) enables the silylative cascade conversion of N-aryl piperidines to sila-N-heterocycles: DFT calculations
The first catalytic access to bridged sila-N-heterocycles from piperidines via cascade sp(3) and sp(2) C-Si bond formation all mediated by a single catalyst B(C6F5)(3) (A) has been recently developed by Park and Chang. Described herein is a theoretical study of the B(C6F5)(3)-catalyzed silylative cascade conversion of N-aryl piperidines (H) to afford polycyclic azasilaheterocycles with a strong emphasis on the dual reactivity of B(C6F5)(3). The DFT calculations show that the catalyzed reaction involves three steps of the cascade reaction: (i) the formation of tetrahydropyridine (I) upon dehydrogenation of the piperidine; (ii) beta -selective hydrosilylation of tetrahydropyridine; (iii) an intramolecular sila-Friedel-Crafts reaction to form a bridged sp(2) C-Si bond. The N-silyl piperidinium borohydride (A ‘) turns out to be the thermodynamically favored, resting species of the overall reaction, which is consistent with the observation of a species such as A ‘ during borane catalysis. The DFT calculations suggest that the beta -selective hydrosilylation of I is the rate-determining step in the entire catalytic cycle, while the liberated I reacts with B(C6F5)(3) to form a zwitterion consisting of iminium and borate units (O). The calculated sila-Friedel-Crafts reactions of a range of presupposed silylated (cyclic)aza intermediates imply the importance of structural integrity on the piperidinyl unit of substrates.
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Reference:
Piperidine – Wikipedia,
,Piperidine | C5H11N – PubChem