135388-39-5

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 

Downstream Products

• 1150576-73-0 methyl 7-hydroxy-2-(3-methoxyphenyl)benzofuran-4-carboxylate 
• 1360260-49-6 1-(3-methoxyphenyl)-2-(2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)ethanone 
• 1402591-63-2 3,3-dimethyl-1-(3-methoxyphenyl)-5-phenyl-4-pentyne-1-one 
• 1402591-79-0 (Z)-5-benzylidene-4,4-dimethyl-3-(3-methoxybenzoyl)dihydrofuran-2(3H)-one 
• 23308-82-9 (R)-(+)-1-(3-methoxyphenyl)-1-ethanol 
• 1612226-12-6 1-(3-methoxyphenyl)-2-((trifluoromethyl)thio)ethanone 
• 1247083-36-8 3,3,3-trifluoro-1-(3-methoxyphenyl)propan-1-one 
• 1644060-34-3 C₁₁H₁₄O₃ 
• 1459246-66-2 4-(3-methoxyphenyl)-4-vinyl-1,3-dioxolan-2-one 
• 87428-52-2 2-hydroxy-3'-methoxyacetophenone 
• 89691-63-4 1-(3-methoxy)-phenylethanol 

Relevant academic research and scientific papers

Photoinduced Deaminative Alkylation for the Synthesis of γ-Ketoesters via Electron Donor–Acceptor Complex Formation

Visible-light-induced deaminative alkylation of Katritzky salts with silyl enol ethers has been developed. The reaction can proceed efficiently through electron donor–acceptor complex formation, avoiding the use of precious metal complexes or synthetically elaborate organic dyes. A series of functionalized γ-ketoesters was successfully obtained with good functional group tolerance and compatibility under mild and straightforward conditions.

Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.

FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers

Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6-tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ-terpinene as a dihydrogen surrogate. A variety of silyl enol ethers undergo efficient hydrogenation, with the reduced products isolated in excellent yields (29 examples, 82 % average yield).

A Solvent-Free Reaction for Silyl Enol Ethers Synthesis

Silyl enol ethers are extremely useful nucleophilic intermediates for chemical transformations because they are synthetically versatile substrates for a wide range of C-C bond-forming reactions. Here, we present a new, mild, and solvent-free procedure for the synthesis of silyl enol ethers that employs a catalytic amount of solid-supported base and an equimolar amount of N, O -(bistrimethylsilyl)acetamide as a silylating agent.

Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.

Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)-C(sp3) Bond Cleavage and Functionalizations

The alkoxyl radical is an important reactive intermediate in mechanistic studies and organic synthesis; however, its current generation from alcohol oxidation heavily relies on transition metal activation under strong oxidative conditions. Here we report the first visible-light-induced alcohol oxidation to generate alkoxyl radicals by cyclic iodine(III) reagent catalysis under mild reaction conditions. The β-fragmentation of alkoxyl radicals enables selective C(sp3)-C(sp3) bond cleavage and alkynylation/alkenylation reactions with various strained cycloalkanols, and for the first time with linear alcohols.

A highly enantioselective hydrogenation of silyl enol ethers catalyzed by chiral frustrated lewis pairs

Using a simple combination of tri-tert-butylphosphine and chiral borane generated in situ by the hydroboration of chiral diene with HB(C 6F5)2 as a frustrated Lewis pair catalyst, a highly enantioselective metal-free hydrogenation of silyl enol ethers was successfully realized to furnish a variety of optically active secondary alcohols in 93-99% yields with 88->99% ees.