Carbonyl reduction with CaH2 and R3SiCl catalyzed by ZnCl2

Abstract

Ketones and aldehydes were effectively reduced by the reaction with CaH 2 and R 3 SiCl in the presence of a catalytic amount of ZnCl 2 . In the absence of the carbonyl substrate, the reagent reduced R 3 SiCl to the corresponding hydrosilane under mild reaction conditions. Leave this area blank for abstract info.

Phosphine-Catalyzed Reductions of Alkyl Silyl Peroxides by Titanium Hydride Reducing Agents: Development of the Method and Mechanistic Investigations

“…Purification by column chromatography (5−10% CH 2 Cl 2 /hexanes) afforded silyl ether 14 as a colorless oil (0.107 g, 66%). A previous literature report does not provide analytical data for the compound: 1 H NMR (500 MHz, CDCl 3 ) δ 3.80 (m, 1H), 1.66 (m, 7H), 1.51 (td, J = 5.8, 11.7 Hz, 4H), 1.43 (m, 3H), 0.95 (t, J = 8.0 Hz, 9H), 0.58 (q, J = 8.0 Hz, 6H); 13 C NMR (125 MHz, CDCl 3 ) δ 72.7, 35.7, 27.6, 25.6, 23.1, 7.1, 5.1; IR (thin film) 2925, 1465, 1238, 1068, 1027, 742 cm −1 ; HRMS (CI) m / z calcd for C 14 H 34 NOSi (M + NH 4 ) + 260.2410, found 260.2405. Anal.…”

Catalytic Synthesis of Silanols from Hydrosilanes and Applications

“…Various hydrosilanes are available commercially and can be prepared by (1) reduction of Si–X (X = halide) or Si–OR (R = alkyl) groups, ,, (2) nucleophilic substitution reaction of chlorohydrosilanes with organometallic reagents, (3) nucleophilic substitution reaction of hexacoordinated silicon species with organomagnesium and organolithium reagents, and (4) catalytic Si–C coupling reaction of dihydrosilanes with aryl halides (Scheme ). − …”

“…Various hydrosilanes are available commercially and can be prepared by (1) reduction of Si−X (X = halide) or Si−OR (R = alkyl) groups, 15,50,51 (2) nucleophilic substitution reaction of chlorohydrosilanes with organometallic reagents, 35 (3) nucleophilic substitution reaction of hexacoordinated silicon species with organomagnesium and organolithium reagents, 52 and (4) catalytic Si−C coupling reaction of dihydrosilanes with aryl halides (Scheme 2). 53−56 For the transformation of hydrosilanes into silanols, water is an ideal oxidant because the side-product is only molecular hydrogen in contrast to other stoichiometric oxidants producing toxic wastes.…”

Hydrodeoxygenation of Carbonyl Compounds Biomass Derivatives Using CaH2 over Pd/C

“…[16] Two years later, in 2007, the same group expanded this work with the system ZnX 2 /CaH 2 /R 3 SiCl for the reduction of a variety of carbonyl compounds. [17] In 2015 the group of Métay and Lemaire reported the reductive alkylation and reductive amination of carbonyl compounds using CaH 2 but this time in combination with supported heterogeneous catalysts of Pd/C and Pt/C respectively. [18] In comparison with other hydrides, CaH 2 is inexpensive, airstable and easy to handle.…”