17745-32-3Relevant articles and documents
Preparation of Functionalized Ketones via Low temperature Grignard Reaction
Eberel, Marcel K.,Kahle, Gerard G.
, p. 2303 - 2304 (1980)
δ-Chloroketones and 5-oxo-9-decenoic acid methyl ester were prepared from 5-chlorovaleryl chloride and methyl 4-(chloroformyl)-butyrate via Grignard reaction in tetrahydrofuran at -70 deg C.
Iron-catalyzed oxidative functionalization of C(sp3)-H bonds under bromide-synergized mild conditions
Yu, Han,Zhao, Qixin,Wei, Zheyu,Wu, Zhikang,Li, Qi,Han, Sheng,Wei, Yongge
supporting information, p. 7840 - 7843 (2019/07/12)
An efficient oxidation and functionalization of C-H bonds with an inorganic-ligand supported iron catalyst and hydrogen peroxide to prepare the corresponding ketones was achieved using the bromide ion as a promoter. Preliminary mechanistic investigations indicated that the bromide ion can bind to FeMo6 to form a supramolecular species (FeMo6·2Br), which can effectively catalyze the reaction.
Combined effects on selectivity in Fe-catalyzed methylene oxidation
Chen, Mark S.,White, M. Christina
scheme or table, p. 533 - 571 (2010/10/05)
Methylene C-H bonds are among the most difficult chemical bonds to selectively functionalize because of their abundance in organic structures and inertness to most chemical reagents. Their selective oxidations in biosynthetic pathways underscore the power of such reactions for streamlining the synthesis of molecules with complex oxygenation patterns. We report that an iron catalyst can achieve methylene C-H bond oxidations in diverse natural-product settings with predictable and high chemo-, site-, and even diastereoselectivities. Electronic, steric, and stereoelectronic factors, which individually promote selectivity with this catalyst, are demonstrated to be powerful control elements when operating in combination in complex molecules. This small-molecule catalyst displays site selectivities complementary to those attained through enzymatic catalysis.
Highly regioselective addition of an ester enolate equivalent to α,β-unsaturated ketones: Selective formation of both isomers derived from 1,2- and 1,4-additions using α-stannyl ester with additives
Yasuda,Matsukawa,Okamoto,Sako,Kitahara,Baba
, p. 2149 - 2150 (2007/10/03)
The reaction of α-stannyl ester with α,β-unsaturated ketones in the presence of stannous chloride (SnCl2) and chlorosilanes (Me3SiCl or Me2SiCl2) gave 1,2- and 1,4-addition products, respectively.
