328086-30-2

Upstream product

• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 536-74-3 phenylacetylene 
• 1066-54-2 trimethylsilylacetylene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 6738-06-3 phenylethynylmagnesium bromide 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 

Downstream Products

• 1262150-92-4 C₃₃H₂₅NO₂ 
• 1262150-93-5 C₂₉H₂₅NO₂ 

Relevant academic research and scientific papers

Gold-Catalyzed Aromatizations of 3-Ene-5-siloxy-1,6-diynes with Nitrosoarenes to Enable 1,4-N,O-Functionalizations: One-Pot Construction of 4-Hydroxy-3-aminobenzaldehyde Cores

This work describes gold-catalyzed aromatizations of 3-ene-5-siloxy-1,6-diynes with nitrosoarenes to form 4-hydroxy-3-aminobenzaldehyde derivatives, manifesting the use of nitrosoarenes as 1,4-N,O-functionalization sources. Various 3-ene-5-siloxy-1,6-diynes in benzoid and nonbenzoid types are applicable substrates. A series of 18O- and 2H-labeling experiments have been conducted to exclude gold-π-alkyne intermediates. We postulate a mechanism of dual gold catalysis involving initial formation of gold-π-alkynylgold species that activates a 1,5-hydrogen shift to form reactive 1,6-dipoles, thus furnishing intramolecular Michael-type reactions with nitrosonium electrophiles.

Gold-Catalyzed Oxidative Cyclizations of { o-(Alkynyl)phenyl propargyl} Silyl Ether Derivatives Involving 1,2-Enynyl Migration: Synthesis of Functionalized 1 H-Isochromenes and 2 H-Pyrans

A new and convenient strategy for the synthesis of functionalized 1H-isochromene and 2H-pyran derivatives based on gold-catalyzed oxidative cyclizations of o-(alkynyl)phenyl propargyl ether derivatives has been developed. The reaction proceeds via gold-catalyzed highly regioselective oxidation, followed by 1,2-migration of an enynyl group and nucleophlic addition. Isocoumarins were also constructed through oxidative cleavage of the exocyclic double bond of the obtained 1H-isochromenes.

Gold-catalyzed Intermolecular Oxidations of 2-Ketonyl-1-ethynyl Benzenes with N-Hydoxyanilines to Yield 2-Aminoindenones via Gold Carbene Intermediates

Gold-catalyzed oxidations of 2-ketonyl-1-ethynyl benzenes with N-hydroxyanilines yield 2-aminoindenone derivatives efficiently. Experimental data suggests that this process involves an α-oxo gold carbene intermediate, generated from the attack of N-hydroxyaniline on furylgold carbene intermediate, rather than the typical attack of oxidants on π-alkynes.

TRACELESS DIRECTING GROUPS IN RADICAL CASCADES: FROM OLIGOALKYNES TO FUSED HELICENES WITHOUT TETHERED INITATORS

The present disclosure is directed to a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by a propargyl alkoxy moiety. Radical translocations lead to the boomerang return of radical center to the site of initial attack where it assists to the elimination of the directing functionality via β-scission in the last step of the cascade. In some aspects, the reaction of the present invention is catalyzed by a stannane moiety, which allows further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions.

Traceless directing groups in radical cascades: From oligoalkynes to fused helicenes without tethered initiators

We report the first example of a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by propargyl OR moiety. Radical translocations lead to the boomerang return of the radical center to the site of initial attack where it assists the elimination of the directing functionality via β-scission in the last step of the cascade. The Bu3Sn moiety continues further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions. (Chemical Equation Presented).

Sequential [3+2] cycloaddition/air oxidation reactions: Triazoloyl ion assisted oxidative cleavage of alkynes

Upon treatment with sodium azide in DMF, bisalkynes undergo chemoselective [3+2] cycloaddition followed by oxidative cleavage of the other alkyne unit by atmospheric oxygen. The neighboring triazoloyl ion is found to assist the cleavage process ultimately to deliver an acid and an aldehyde. Cycloaddition of azide with a bisalkyne chemoselectively forms a triazole, which subsequently undergoes oxidative cleavage by atmospheric oxygen to yield a carboxylic acid and an aldehyde. The mechanism for this reaction is investigated in depth. Copyright

Highly regioselective synthesis of 1,3-diiodonaphthalene derivatives via a sequential cascade iodocyclization

A novel and flexible sequentially cascade iodocyclization for the synthesis of highly substituted 1,3-diiodinated naphthalene derivatives in up to 99% yield under mild conditions is reported. The dihalogenated moiety can be readily introduced into the naphthalenes in a position that is usually not easily functionalized.

Synthesis of 2-azaanthracenes via a sequential Sonogashira coupling/alkynyl imine-allenyl imine isomerization/aza-Diels-Alder/elimination-aromatization reaction

An interesting sequential Sonogashira coupling/alkynyl imine-allenyl imine isomerization/aza-Diels-Alder/elimination-aromatization reaction, providing a facile synthesis of substituted 2-azaanthracenes from 1,6-diynes and imidoyl chlorides, is reported. T

Scope of the thermal cyclization of nonconjugated ene-yne-nitrile system: A facile synthesis of cyanofluorenol derivatives

Thermal cyclizations of nonconjugated ene-diyne-nitrile 1 and ene-triyne-nitrile 2 systems were examined and proved to yield not azafluorenol. but cyanofluorenol derivatives (9 and 11, respectively), indicating that the cyano groups do not participate in the radical cycloaromatization but do play important roles to determine the mode of cyclization. Copyright

Synthesis of indenyl ethers by gold(I)-catalyzed intramolecular carboalkoxylation of alkynes

The gold(I)-catalyzed carboalkoxylation of alkynes to form indanone derivatives from readily available ortho-acetylenic benzylic ethers is described. Importantly, the gold(I)-catalyzed rearrangement of enantioenriched benzylic ethers proceeds with chirali