19082-37-2

Upstream product

• 96-09-3 styrene oxide 
• 74-99-7 prop-1-yne 
• 18498-59-4 4-pentyn-1-al 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 100-52-7 benzaldehyde 
• 5390-04-5 pent-1-yn-5-ol 
• 18476-65-8 1-phenylpenta-4-yn-1-one 
• 1823-14-9 5-phenyl-1-pentyne 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 92190-57-3 ethyl(2-benzoylpent-4-ynoate) 

Downstream Products

• 18476-65-8 1-phenylpenta-4-yn-1-one 
• 141089-33-0 1-phenylhexa-4,5-dien-1-ol 
• 1208003-53-5 2-(3-hydroxy-3-phenylpropyl)-2-methyl-1,2,3,4-tetrahydro-4-quinazolinone 
• 1349762-57-7 benzyl 7-hydroxy-7-phenylhepta-2,3-dienoate 
• 58193-48-9 1-phenyl-1-hydroxy-pentane-4-one 
• 1232199-42-6 5-iodo-2-phenyl-3,4-dihydro-2H-pyran 
• 101321-34-0 2-methylene-5-phenyl-tetrahydrofuran 
• 126594-11-4 2-<1-<(trimethylsilyl)oxy>-1-phenyl-4-pentynyl>-1,3-dithiane 
• 126594-10-3 2-(hydroxy-1-phenyl-4-pentynyl)-1,3-dithiane 
• 887946-58-9 1-((E)-5-bromo-1-phenylpent-4-enyloxy)-2,2,6,6-tetramethyl-piperidine 
• 887946-59-0 2,2,6,6-tetramethyl-1-(1-phenylpent-4-ynyloxy)piperidine 
• 887946-74-9 (1-bromo-pent-4-ynyl)-benzene 

Relevant academic research and scientific papers

Dibrominative Spirocyclization of 2-Butynolyl Anilides: Synthesis of gem-Dibromospirocyclic Benzo[ d][1,3]oxazines and Their Application in the Synthesis of 4 H-Furo[3,2- b]indoles

The combination of catalytic aqueous hydrochloric acid (HCl) and N-bromosuccinimide (NBS) generated electrophilic bromine monochloride (BrCl), which readily induced spiroannulation of 2-alkynolyl anilides (n = 1-3) to form gem-dibromospirocyclic benzo[d][

Synthesis of Benzylic Alcohols by C-H Oxidation

Selective methylene C-H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals.

Lewis acid catalyzed cascade annulation of alkynols with α-ketoesters: A facile access to γ-spiroketal-γ-lactones

A novel Lewis acid catalyzed intermolecular cascade annulation of alkynols with α-ketoesters has been developed. This simple and efficient cascade annulation proceeds through a 5-exo-dig cyclization of alkynols followed by annulation with α-ketoester to provide a wide variety of unsaturated γ-spiroketal-γ-lactones (1,6-dioxaspiro[4.4]non-3-en-2-ones) related to many natural products.

Dual cobalt-copper light-driven catalytic reduction of aldehydes and aromatic ketones in aqueous media

We present an efficient, general, fast, and robust light-driven methodology based on earth-abundant elements to reduce aryl ketones, and both aryl and aliphatic aldehydes (up to 1400 TON). The catalytic system consists of a robust and well-defined aminopyridyl cobalt complex active for photocatalytic water reduction and the [Cu(bathocuproine)(Xantphos)](PF6) photoredox catalyst. The dual cobalt-copper system uses visible light as the driving-force and H2O and an electron donor (Et3N or iPr2EtN) as the hydride source. The catalytic system operates in aqueous mixtures (80-60% water) with high selectivity towards the reduction of organic substrates (>2000) vs. water reduction, and tolerates O2. High selectivity towards the hydrogenation of aryl ketones is observed in the presence of terminal olefins, aliphatic ketones, and alkynes. Remarkably, the catalytic system also shows unique selectivity for the reduction of acetophenone in the presence of aliphatic aldehydes. The catalytic system provides a simple and convenient method to obtain α,β-deuterated alcohols. Both the observed reactivity and the DFT modelling support a common cobalt hydride intermediate. The DFT modelled energy profile for the [Co-H] nucleophilic attack to acetophenone and water rationalises the competence of [CoII-H] to reduce acetophenone in the presence of water. Mechanistic studies suggest alternative mechanisms depending on the redox potential of the substrate. These results show the potential of the water reduction catalyst [Co(OTf)(Py2Tstacn)](OTf) (1), (Py2Tstacn = 1,4-di(picolyl)-7-(p-toluenesulfonyl)-1,4,7-triazacyclononane, OTf = trifluoromethanesulfonate anion) to develop light-driven selective organic transformations and fine solar chemicals.

Sodium amalgam mediated desulfonylative reduction of α-functionalized β-ketosulfones

Sodium amalgam mediated desulfonylative reduction of β-ketosulfones in MeOH at rt affords alcohols in good yields via radical desulfonylation of β-ketosulfones and sequential Bouveault-Blanc reduction of the resulting ketones.

Enantioselective preparation of 8-oxabicyclo[3.2.1]octane derivatives via asymmetric [3+2]-cycloaddition of platinum-containing carbonyl ylides with vinyl ethers

A catalytic asymmetric synthesis of 8-oxabicyclo[3.2.1]octane derivatives was achieved through the [3+2]-cycloaddition of the platinum-containing carbonyl ylides generated from acyclic γ,δ-ynones on treatment with 10 mol % of PtCl2-Walphos and

Stereoselective synthesis of medium-sized cyclic compounds through the intramolecular michael-type reaction utilizing alkyne-hexacarbonyldicobalt complex formation

Alkyne-hexacarbonyldicobalt complexes having silyl enol ether and electron-deficient alkene moieties on opposite ends were treated with MeAlCl2 in the presence of 2,6-di-t-butylpyridine in CH 2Cl2 to give synthetically use

Isonitrile trapping reactions under thermolysis of alkoxyamines for the synthesis of quinolines

An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R1, oxidation to dihydro-1H-cyclopenta- [b]quinolines (for R1 = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R1 = CO2Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.

Aminoalkynyldithianes. A new class of calcium channel blockers

Several dithiane derivatives, prepared as intermediates for compounds structurally related to the therapeutically useful antimuscarinic agent oxybutynin, were effective inhibitors of calcium ion induced contraction of guinea pig ileal strips and of KCl-in

Regiospecific functionalisation of unsaturated compounds via their dilithio derivatives. Part 1: Reaction of dilithio compounds of 1-alkynes with epoxides, benzyl halides and trimethylchlorosilane

Acetylenes HCC-CH2-R (R = H, alkyl) have been converted with good yields into their derivatives HCC-CH(E)-R (E = -CH2CHR'OH, -CH2Ph, -SiMe3) by reaction of the dilithio compound LiCC-CH(Li)-R with epoxides OC2H3-R' (R' = H, Ph), benzyl chloride and trimethylchlorosilane (TMSCl), respectively.