13950-58-8

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 789-25-3 HSiPh₃ 

Downstream Products

• 463-51-4 Ketene 
• 1516-80-9 ethoxytriphenylsilane 
• 88842-13-1 (Z-)-ethyl 5-phenylpent-2-enoate 
• 55282-95-6 ethyl (2E)-5-phenylpent-2-enoate 
• 4610-69-9 (Z)-ethyl cinnamate 
• 4192-77-2 ethyl cinnamate 
• 936005-43-5 C₂₂H₂₃O₂SiN 
• 936005-52-6 C₃₇H₃₈O₈Si 
• 936005-48-0 C₃₇H₄₀O₅Si 
• 936005-47-9 C₂₇H₂₈O₃Si 
• 936005-50-4 C₃₇H₃₈O₅Si 
• 936005-49-1 C₂₇H₂₆O₃Si 
• 936005-46-8 C₂₃H₂₂O₂Si 
• 1026594-58-0 C₂₃H₂₆O₂Si 

Relevant academic research and scientific papers

Cyclobutadiene cobalt complexes as catalysts for insertion of diazo compounds into X–H bonds

Novel cyclobutadiene cobalt complex with labile naphthalene ligand [(C4Et4)Co(C10H8)]PF6 catalyzes the insertion of ethyl diazoacetate into X–H bonds giving the corresponding products in 15–75% yields

Engineering catalytic coordination space in a chemically stable Ir-porphyrin MOF with a confinement effect inverting conventional Si-H insertion chemoselectivity

An iridium-porphyrin ligand, Ir(TCPP)Cl (TCPP = tetrakis(4-carboxyphenyl)porphyrin), has been utilized to react with HfCl4 to generate a stable Ir(iii)-porphyrin metal-organic framework of the formula [(Hf6(μ3-O)8(OH)2(H2O)10)2(Ir(TCPP)Cl)3]·solvents (Ir-PMOF-1(Hf)), which possesses two types of open cavities (1.9 × 1.9 × 1.9 and 3.0 × 3.0 × 3.0 nm3) crosslinked through orthogonal channels (1.9 × 1.9 nm2) in three directions. The smaller cavity is surrounded by four catalytic Ir(TCPP)Cl walls to form a confined coordination space as a molecular nanoreactor, while the larger one facilitates reactant/product feeding and release. Therefore, the porous Ir-PMOF-1(Hf) can act as a multi-channel crystalline molecular flask to promote the carbenoid insertion reaction into Si-H bonds, featuring high chemoselectivity towards primary silanes among primary, secondary and tertiary silanes under heterogeneous conditions that are inaccessible by conventional homogeneous catalysts.

Silver-catalyzed silicon-hydrogen bond functionalization by carbene insertion

The catalytic functionalization of silicon-hydrogen bonds by means of the insertion of carbene units:CHCO2Et from ethyl diazoacetate (EDA) has been achieved using a silver-based catalyst, constituting the first example of this metal to promote this transformation. Competition experiments have revealed that the relative reactivity of substituted silanes depends on the bond dissociation energy of the Si-H bond (tertiary > secondary > primary for ethyl substituted). In the presence of bulky substituents such order reverts to secondary > primary ≈ tertiary (for phenyl substituted). Screening with other diazo compounds has shown that N2C(Ph)CO2Et displays similar reactivity to that of EDA, whereas other N2C(R)CO 2Et (R = Me, CO2Et) gave lower conversions. The Royal Society of Chemistry 2013.

Synthesis of α-(alkoxysilyl)acetic esters. A route to 1,2 diols

An easy route to α-(alkoxysilyl)acetic esters and their utilization is described. It involves a two-step sequence carried out in one pot Rhodium catalyzed Si-H insertion of a carbenoid, generated by decomposition of N2CHCO2Et, followed by a nucleophilic attack onto the Si-Cl bond by an alcohol. Alkylation of the title esters, reduction of the ester function and finally oxidation of the C-Si bond provide a facile entry to 1,2 diols.

A New and General Synthesis of α-Silyl Carbonyl Compounds by Si-H Insertion from Transition Metal Catalyzed Reactions of Diazo Esters and Diazo Ketones

α-Silyl esters and α-silyl ketones are formed in high yield by Rh2(OAc)4- or Cu(acac)2-catalyzed decomposition of diazo esters and diazo ketones in the presence of organosilanes.