1276992-80-3Relevant academic research and scientific papers
Mono(hydrosilylation) of N-Heterocycles Catalyzed by B(C6F5)3and Silylium Ion
Nikonov, Georgii I.,Petrushko, William D.
, p. 4717 - 4722 (2020)
Catalytic hydrosilylations of various N-heterocycles mediated by silylium ion and electrophilic borane catalysts are reported. The reactions proceed via intermediate silylquinolinium ions that give rise to a variety of reduced and coupling products. Generally, highly selective 1,4-regioselectivity is observed.
Catalytic 1,4-selective hydrosilylation of pyridines and benzannulated congeners
Koenigs, C. David F.,Klare, Hendrik F. T.,Oestreich, Martin
supporting information, p. 10076 - 10079 (2013/10/01)
Radically different! The hydrosilylation of pyridines and quinolines is strictly 1,4-selective and likely involves an ionic one-step rather than the established radical two-step hydride transfer from a ruthenium(II) hydride complex onto the respective pyridinium and quinolinium ion intermediates (see scheme; ArF=3,5-(CF3)2C6H 3). Even 4-substituted substrates react highly regioselectively. Isoquinolines yield the 1,2-reduced heterocycles.
Chemo- and regioselective catalytic reduction of N-heterocycles by silane
Lee, Sun-Hwa,Gutsulyak, Dmitry V.,Nikonov, Georgii I.
supporting information, p. 4457 - 4464 (2013/09/23)
The ruthenium complex [Cp(iPr3P)Ru(NCCH3) 2]+ (1) catalyzes the regioselective hydrosilylation of pyridines to 1,4-dihydropyridines. Substitution in the 3- and 5-positions is tolerated, whereas pyridines with substituents in the 2-, 4-, and 6-positions are not reduced. Reduction of functionalized pyridines having keto and ester substituents results in a mixture of products. N-Silyl-1,4-dihydropyridine reacts with ketones and aldehydes to give products of N-Si addition across the C=O bond. Hydrosilylation of pyridine in acetone results quantitatively in the addition product PhMe2SiO-CMe2-NC5H 6, which decomposes in hexane to give the parent dihydropyridine HNC5H6. The phenanthroline complex [Cp(phen)Ru(NCCH 3)2]+ (10) catalyzes regioselective 1,4-reduction of phenanthroline by a 3-4-fold excess of silane/water or silane/alcohol mixtures. The Cp* analogue [Cp*(ph n)Ru(NCCH 3)2]+ (9) catalyzes 1,4-regioselective monohydrosilylation of phenanthroline, quinoline, acridine, and 1,3,5-triazine and the 1,2-reduction of isoquinoline. In contrast, 2-substituted phenanthroline, pyrazine, 2-ethylpyridine, 2,6-lutidine, 2,4-lutidine, and pyrimidine are not reduced under these conditions by either of the catalysts studied.
Facile catalytic hydrosilylation of pyridines
Gutsulyak, Dmitry V.,Van Der Est, Art,Nikonov, Georgii I.
supporting information; experimental part, p. 1384 - 1387 (2011/04/21)
Not only surprisingly facile, a hydrosilylation of pyridines under the catalysis of [Cp(iPr3P)Ru(NCCH3)2]+ has the advantages that it is 1,4-regioselective and reversible. The products can be transformed in a variety of ways (see scheme). The related complex [CpRu(NCCH3)3]+ catalyzes the two-hydrogen-atom reduction of phenanthroline by HSiMe2Ph/water.
