819871-77-7

Upstream product

• 6630-33-7 ortho-bromobenzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 1530-33-2 isopropyltriphenylphosphonium bromide 

Downstream Products

• 1322670-31-4 1-(2-methylprop-1-en-1-yl)-2-(prop-1-yn-1-yl)benzene 
• 1562-94-3 4,4'-dimethoxyazoxybenzene 
• 1443260-24-9 4-methyl-N-(3-(prop-1-en-2-yl)-2,3-dihydro-1H-inden-1-ylidene)benzenesulfonamide 

Relevant academic research and scientific papers

Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.

Diisobutylaluminum hydride promoted cyclization of o -(trimethylsilylethynyl)styrenes to indenes

The reaction of o-(trimethylsilylethynyl)styrenes with diisobutylaluminum hydride (DIBAL-H) provides 2-trimethylsilyl-1H-indenes efficiently. The cyclization mechanism involves regioselective hydroalumination of the alkynyl moiety, geometrical isomerizati

Silver-catalyzed stereoselective [3+2] cycloadditions of cyclopropyl-indanimines with carbonyl compounds

Silver-catalyzed stereoselective [3+2] cycloadditions between mono-substituted cyclopropyl-indanimines and aldehydes are reported. The stereochemical course of the reaction is rationalized with a cyclic transition state. The resulting indanimine cycloadducts are not readily hydrolyzed unless external aldehydes are present with the silver catalyst. Notably, this hydrolysis process leads to a change of stereochemistry for the resulting indanone products. Copyright

Gold-catalyzed cyclization/oxidative [3+2] cycloadditions of 1,5-enynes with nitrosobenzenes without additional oxidants

Golden control: The title reaction (see scheme) proceeds with high stereocontrol to generate the heterocyclic products in good yield. Experiments to probe the mechanism were performed. Copyright

Nature of the intermediates in gold(I)-catalyzed cyclizations of 1,5-enynes

The carbene or carbocationic nature of the intermediates in the gold-catalyzed cycloisomerization of 1,5-enynes can be revealed, depending on the ligands on the gold catalysts. Gold complexes with highly electron-donating ligands promote reactions that proceed via intermediates with carbene-like character, leading to products with a bicyclo[3.1.0]hexene skeleton. The intermediate cyclopropyl endo-gold carbenes formed in this cyclization have been trapped, for the first time, to give biscyclopropane derivatives in a reaction that proceeds in a concerted fashion, according to DFT calculations.

Rutheniun-catalyzed cycloisomerization of o-(ethynyl)phenylalkenes to diene derivatives via skeletal rearrangement

Treatment of a series of 2′,2′-disubstituted (oethynyl)styrenes with TpRu(PPh3)(CH3CN)2PF6 (10 mol %) in benzene (80°C, 12-18 h) efficiently gave 2-alkenyl-1H-indene derivatives. This catalytic reaction represents an atypical enyne cycloisomerization with skeletal rearrangement of starting enyne, where the C=C bond is completely cleaved and inserted by the terminal alkynyl carbon. The reaction mechanism was elucidated by a series of deuterium and 13C labeling experiments, as well as by changing the substituents at the phenyl moieties. The mechanism is proposed to involve the following key steps: 5-endo-dig cyclization of ruthenium-vinylidene intermediate, a nonclassical ion formation, and the "methylenecyclopropane-trimethylenemethane" rearrangement.

Ruthenium-catalyzed cyclization of epoxide with a tethered alkyne: Formation of ketene intermediates via oxygen transfer from epoxides to terminal alkynes

Treatment of (o-ethynyl)phenyl epoxides with TpRuPPh3(CH 3CN)2PF6 (10 mol %) in hot toluene (100 °C, 3-6 h) gave 2-naphthols or 1-alkylidene-2-indanones very selectively with isolated yields exceeding 72%, depen